EP3589787A1

EP3589787A1 - Aromatized and flavored paper products

Info

Publication number: EP3589787A1
Application number: EP18761171.0A
Authority: EP
Inventors: Gil LUXENBOURG; Daniela Ilieva Batovska; Jualian Simeonov Karadjov; Raphael Luxenbourg
Original assignee: Iiw Entourage Delivery Systems Ltd
Current assignee: Iiw Entourage Delivery Systems Ltd
Priority date: 2017-03-02
Filing date: 2018-03-01
Publication date: 2020-01-08
Also published as: WO2018158774A1; CN110382777A; EP3589787A4; CA3054269A1

Abstract

The present invention relates to paper products, inter alia, smoking paper products, stably enriched with aroma and/or flavor compounds. More particularly, the invention relates to paper products enriched with a terpene profile, mimicking flavor and/or aroma of a cannabis plant.

Description

AROMATIZED AND FLAVORED PAPER PRODUCTS

FIELD OF THE INVENTION

BACKGROUND

Terpenes are hydrocarbons occurring widely in plants and animals and built up from isoprene (i.e., C5¾) units. Terpenoids are regarded as modified terpenes, for example, when methyl groups are moved or removed, or when oxygen atoms added. The term "terpenes", in many occasions is used to broadly include terpenoids.

Terpenes are typically present in small amounts in living organisms, where they play numerous vital roles in plant physiology as well as important functions in cellular membranes.

Terpenes are naturally formed by the combination of two molecules of acetic acid to give mevalonic acid (C6H12O4) and conversion of the latter to isopentenyl pyrophosphate, which contains the five-carbon isoprene skeleton. Additional transformations of the isopentenyl compound yield the various terpenes and terpenoids.

Terpenes are typically classified according to the number of isoprene units in the molecule. Monoterpenes (C₁₀H₁₆) contain two isoprene units, sesquiterpenes (C15H24) contain three, diterpenes (C20H32) contain four, triterpenes (C30H48) contain six, and tetraterpenes (C40H64) contain eight isoprene units. Polyterpenes (a.k.a. rubber and gutta-percha) contain 1,000-5,000 isoprene units, joined together to form a long chain. Monoterpenes, sesquiterpenes, and diterpenes are abundant in essential oils of plants.

Terpenes possess desirable properties for use in food, cosmetic, pharmaceutical and biotechnology industries.

The present invention pertains to a novel and advantageous use of those compounds in paper products. SUMMARY OF THE INVENTION

Objects of the invention are achieved by providing a paper product, such as, a smoking rolling paper enriched with aroma and/or flavor compounds. Objects of the invention are achieved by providing a rolling paper stably enriched with two or more terpene and/or terpenoid compounds.

Thus, an aspect of the invention pertains to a paper product infused with an effective amount of a composition comprising at least one of: a flavor compound and an aroma compound. In one or more embodiments, the aroma compound and/or flavor compound originates from a plant, such as a cannabis plant. In one or more embodiments, the aroma compound and/or flavor compound is a terpene and/or a terpenoid. In one or more embodiments, the aroma compound and/or flavor compound is a synthetic compound. In one or more embodiments, the paper products further comprise a fixative agent. In one or more embodiments, the fixative agent affords or mediates binding or incorporation of the flavor and/or aroma compound within the paper product. In one or more embodiments, the paper products further comprise an antioxidant agent. In one or more embodiments, the antioxidant agent reduces or prevents oxidation of the terpenes and terpenoids, resulting with an enhanced stability of the aroma and/or flavor of the paper products.

In a further aspect, the present invention provides an aromatized and/or flavored paper product, the paper product comprising, one or more terpene(s) and/or one or more terpenoid(s), and at least one of a fixative agent and an antioxidant.

In one or more embodiments, the terpene and/or terpenoid is maintained in the paper product for a substantially longer time as compared to a paper product without a fixative agent and an antioxidant.

In one or more embodiments, the antioxidant is selected from the group consisting of: butylated hydroxy anisole, butylated hydroxytoluene, cannabidiol, propyl gallate, tertiary butylhydroquinone, tocopherol, vitamin E, and any combination thereof.

In one or more embodiments, the fixative agent is characterized by at least one of: oil solubility, binding capacity to cellulose, biding capacity to terpene and/or terpenoid, non-toxicity, flavorless, odorless, or any combination thereof.

In one or more embodiments, the fixative agent is selected from the group consisting of: a polypropylene glycol, a PPG-20 Methyl Glucose Ether, 1,3-butanedeiol, triethyl citrate, and any combination thereof. In one or more embodiments, the polypropylene glycol is having a M.W. of about 160 Da to about 10,000 Da. In one or more embodiments, the polypropylene glycol is having a M.W. selected from about 160 Da to about 400, and about 4,000 to about 10,000 Da.

In one or more embodiments, the terpene and/or the terpenoid is provided as a natural cannabis plant extract.

In one or more embodiments, the terpene and/or the terpenoid is an isolated terpene and/or the terpenoid. In one or more embodiments, the terpene and/or the terpenoid is a synthetic compound.

In one or more embodiments, the paper product is a smoking paper product. In one or more embodiments, the smoking paper product is selected from a rolling paper, a tip and a filter.

In one or more embodiments, the paper is porous presenting pores having a diameter of about lxlO^"3 μπι to about 2xl0^~3 μπι. In one or more embodiments, the paper product is manufactured by applying onto the paper a composition comprising one or more terpene(s) and/or one or more terpenoid(s), and at least one of a fixative agent and an antioxidant. In one or more embodiments, the one or more terpene(s) and/or one or more terpenoid(s) is present within the composition in an amount of about 45% to about 55%, by weight of the composition. In one or more embodiments, the antioxidant is present within the composition in an amount of about 0.1 % to about 2% by weight of the composition. In one or more embodiments, the fixative agent is present within the composition in an amount of about 45% to about 55% by weight of the composition. In one or more embodiments, the weight ratio between the fixative agent and the terpene and/or terpenoid is about 3: 1 to about 1:3. In one or more embodiments, the ratio is about 1 : 1. In one or more embodiments, evaporation of the terpene and/or terpenoid is substantially reduced as compared to a paper product without a fixative agent and an antioxidant. In one or more embodiments, the overall amount of the terpene and/or terpenoid remains within the paper for at least about 10 minutes following exposure of the paper to the environment.

In one or more embodiments, the paper product comprises a terpene and/or terpenoid profile presenting substantial similarity to the terpene and/or terpenoid profile present naturally within a cannabis strain. In one or more embodiments, the profile is stably maintained for at least about 10 minutes at ambient environment. In one or more embodiments, at least about 50% of the terpenes/terpenoids molecule types remain in the paper product, following 5 minutes exposure to ambient air.

In one or more embodiments, the paper further comprises a cellulose coat provided on top of said paper product. In one or more embodiments, the paper product is manufactured by applying pressure onto the paper following applying the terpenes/terpenoids composition. In one or more embodiments, the pressure is about lOOg/sq inch to about 5000g/sq.

In one or more embodiments, the terpene(s) and/or terpenoid(s) is present in the paper product in an amount of about 0.2 mg/cm² to about 1 mg/cm².

In one or more embodiments, the fixative agent is present in the paper product in an amount of about 0.2 mg/cm² to about 1 mg/cm².

In yet a further aspect, the present invention provides a method of producing an aromatized and/or flavored paper product, the method comprising

preparing a composition comprising one or more terpene(s) and/or one or more terpenoid(s); applying the composition onto the paper product;

applying pressure onto the paper product; and

removing excess of the composition from the paper product; thereby manufacturing an aromatized and/or flavored paper product.

In one or more embodiments, the composition further comprises at least one of a fixative agent and an antioxidant.

In one or more embodiments, the method further comprises applying a cellulose layer over said paper product after removing excess of the terpene(s) and/or terpenoid(s) composition. In one or more embodiment, the step of applying the composition onto the paper product occurs concomitantly to applying pressure onto the paper product.

In one or more embodiments, the method further comprises packing the paper product within a hermetically sealed package.

In one or more embodiments, applying pressure is conducted using a roller. In one or more embodiments, the pressure is within the range of about lOOg/sq inch to about 5000g/sq inch. In one or more embodiments, the paper product is a smoking paper product. In one or more embodiments, the smoking paper product is selected from a rolling paper, a tip and a filter. In one or more embodiments, the smoking paper product is a rolling paper and wherein applying the composition onto the paper product is conducted on both sides of the rolling paper.

Yet a further aspect of the invention pertains to a method of producing the herein disclosed aroma and/flavor compound-enriched paper product, the method comprising: preparing a composition comprising predetermined amounts of an aroma and/or a flavor compound; applying a predetermined amount of the composition on one side of the paper, spreading the composition onto the paper product, and inserting the composition within the paper product. In one or more embodiments, the methods comprise applying an amount of the composition on the other side of the paper, and spreading the composition on top of the paper, optionally with a fibrous pad or a roller. In one or more embodiments, inserting the composition within the paper is made by physical means, such as by pressure, to thereby press and insert the composition into the pores of the paper. In one or more embodiments, the method further comprises packing the terpene/terpenoid enriched paper. In one or more embodiments, the method further comprises sealing the package.

Unless otherwise defined, all technical or/and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which the invention pertains. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of embodiments of the invention, exemplary methods or/and materials are described below. In case of conflict, the patent specification, including definitions, will control. In addition, the materials, methods, and examples are illustrative only and are not intended to be necessarily limiting.

BRIEF DESCRIPTION OF THE DRAWINGS

Some embodiments of the invention are herein described, by way of example only, with reference to the accompanying drawings. With specific reference now to the drawings in detail, it is stressed that the particulars shown are by way of example and for purposes of illustrative discussion of embodiments of the invention. In this regard, the description taken with the drawings makes apparent to those skilled in the art how embodiments of the invention may be practiced.

In the drawings:

FIG. 1 is a line graph showing the average weight percent differences between rolling papers incorporated with a composition comprising terpenes, a fixative agent and an anti-oxidative agent (a striped line), rolling papers incorporated with a composition comprising terpenes in a comparable amount but without a fixative agent and an anti-oxidative agent (a dotted line), and rolling papers incorporated with a composition comprising terpenes in half the amount (a full line); according to some embodiments of the invention; FIG. 2 is a line graph showing relative amounts of terpenes and terpenoids in a paper product comprising a terpene/terpenoid composition; according to some embodiments of the invention;

FIG. 3 is a line graph showing relative amounts of terpenes and terpenoids in a paper product comprising terpene/terpenoid composition that comprises a fixative agent and an antioxidant agent; according to some embodiments of the invention.

DETAILED DESCRIPTION OF THE INVENTION

It is understood that the invention is not limited to the particular methodology, protocols, and reagents, etc., described herein, as these may vary as the skilled artisan will recognize. It is also to be understood that the terminology used herein is used for the purpose of describing particular embodiments only and is not intended to limit the scope of the invention. The following exemplary embodiments may be described in the context of exemplary embolization procedures for ease of description and understanding. However, the invention is not limited to the specifically described products, compositions, devices and methods, and may be adapted to various applications without departing from the overall scope of the invention. All ranges disclosed herein include the endpoints. The use of the term "or" shall be construed to mean "and/or" unless the specific context indicates otherwise.

The present invention provides novel smoking products comprising flavor and/or aroma compounds. The present invention is particularly useful for smoking products and provides, for example, rolling papers that are flavored and/or aromatized with a flavor and/or aroma compounds.

Terpenes and terpenoids are known in their relatively high volatile characteristics. Accordingly, in typical cases, terpenes or terpenoids will rapidly evaporate to air when applied onto products. The present invention overcomes this obstacle by adding an agent (hereinafter referred to as "a fixative agent") that affords stability and enhances retention of the terpene/terpenoid within the paper product.

Advantageously, the aroma and/or flavor compounds are stably maintained within the product, even following exposure to the environment or while smoking (i.e., upon burning the paper).

Further advantageously, the herein disclosed products provide an improved smell, and/or flavor and increase the smoking experience effect. Further advantageously, the paper products are incorporated with terpene and/or terpenoid profile which is substantially similar (in the types of molecules and/or the ratio between the molecules) to terpene and/or terpenoid profile present naturally in a cannabis plant. Such similar terpene/terpenoid profile mimics the flavor and/or aroma of natural cannabis plant.

As used herein the term "terpene and/or terpenoid profile" refers to an assembly of at least two types of terpene and/or terpenoid molecules being substantially similar to the types of terpene and/or terpenoid molecules present naturally in a cannabis plant.

In an embodiment of the invention, the term refers to several types of terpene and/or terpenoid molecules in the profile. For example, 5 or more, or 10 or more, or 20 or more terpene and/or terpenoid molecules. In an embodiment of the invention, the term relates to the ratio between terpenes and/or terpenoids molecules (i.e., molar or weight ratio). In an embodiment of the invention, the ratio between molecules in the terpene and/or terpenoid profile is substantially similar to the ratio between terpene and/or terpenoid molecules present naturally in a cannabis plant.

The invention is based in part on the unexpected discovery that, compositions, that comprise, in addition to terpenes and terpenoids, a fixative agent and/or an antioxidant agent, and/or that were infused with terpenes and terpenoids while applying pressure, present an improved retention and/or stability of the terpenes and/or terpenoids within the paper.

As used herein the term "stability" refers to a terpene and/or terpenoid profile maintained substantially stable in the paper product. In an embodiment of the invention, the herein disclosed paper products present significantly higher stability for longer time periods as compared to comparable paper product without an antioxidant and/or a fixative agent, and/or that wasn't infused with terpene and/or terpenoid while applying pressure. In an embodiment of the invention, the terpenes/terpenoids profile exhibits substantial stability for at least about 3 minutes, 5 minutes, at least about 10 minutes or at least about 15 minutes, at least about 20 minutes, at least about 30 minutes, or any value in between. Each possibility presents a separate embodiment of the invention. In an embodiment of the invention, the terpenes/terpenoids profile exhibits stability for at least about 5 minutes, and up to about 90 minutes. For example, at least about 5 minutes and up to about 80 minutes, or at least about 10 minutes and up to about 70 minutes, or at least about 10 minutes and up to about 60 minutes, at least about 5 minutes and up to about 50 minutes, or at least about 5 minutes and up to about 40 minutes, or at least about 5 minutes and up to about 30 minutes, or any time periods in between. Each possibility presents a separate embodiment of the invention.

In an embodiment of the invention, at least about 50% of the terpenes/terpenoids molecule types

(irrespective of the overall terpenes/terpenoids quantity) remain in the paper product, following exposure to ambient air, for at least about 3 minutes, 5 minutes, 10 minutes, 15 minutes, 20 minutes, 25 minutes, 30 minutes, 35 minutes, 40 minutes, 45 minutes, 50 minutes, 55 minutes, 60 minutes, 65 minutes, 70 minutes, 75 minutes, 80 minutes, 85 minutes, or about 90 minutes, or any value in between. Each possibility presents a separate embodiment of the invention. For example, at least about 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, or 95% of the terpenes/terpenoids types of molecules remain in the paper product, following exposure to ambient air, for at least about 5 minutes, 10 minutes, 15 minutes, 20 minutes, 25 minutes, 30 minutes, 35 minutes, 40 minutes, 45 minutes, 50 minutes, 55 60 minutes, 65 minutes, 70 minutes, 75 minutes, 80 minutes, 85 minutes, or about 90 minutes. Each possibility presents a separate embodiment of the invention.

Without being bound by any theory or mechanism of action, the enhanced stability is due to the addition of a fixating agent and/or antioxidant and/or due to applying pressure when manufacturing the paper product. In accordance with this embodiment, the term "comparable paper product" refers to a compound comprising similar amounts of aroma and/or flavor compound and without a fixating agent and/or without an antioxidant and/or without an antioxidant, and/or that wasn't manufactured while applying pressure on the paper following spreading the terpene/terpenoid composition.

In one or more embodiments, the herein disclosed products present enhanced maintenance in the paper which is significantly higher than a corresponding product containing an essentially similar amount of flavor and/or aroma compounds but do not contain an antioxidant and/or an antioxidant and/or a fixating agent. In one or more embodiments, the term "significantly higher" encompasses at least about 1.2, 1.5 folds, or at least 2 folds more. Each possibility presents a separate embodiment of the invention.

As used herein the term "retention" refers to the overall amount of aroma and/or flavor compounds that remain for substantially longer duration in the paper product as compared to comparable paper product without an antioxidant and/or a fixative agent, and/or that wasn't infused with terpene and/or terpenoid while applying pressure. In an embodiment of the invention, retention refers to the entire terpene/terpenoid molecules maintained for longer period in a paper product (i.e., presents a reduced evaporation) as compared to a comparable paper without an antioxidant and/or a fixative agent, and/or that wasn't infused with terpene and/or terpenoid while applying pressure. In an embodiment of the invention, the terpenes/terpenoids exhibits substantial enhanced retention for at least about 5 minutes, at least about 10 minutes, at least about 15 minutes, at least about 20 minutes, at least about 25 minutes, or at least about 30 minutes, or at least about 40 minutes, or at least about 50 minutes, or at least about 60 minutes, or any value in between.

In an embodiment of the invention, the overall quantity of the terpenes/terpenoids exhibits retention of at least about 20% for 90 minutes or above at ambient air. For example, at least about 50%, or 60%, or 70%, or 80% of the overall terpenes/terpenoids is still infused at about 5 minutes or above, or at about 10 minutes or above. In an embodiment of the invention, at least about 50% of the overall terpenes/terpenoids is still infused at about 20 minutes or above, or at least about 40% of the overall terpenes/terpenoids is still infused at about 30 minutes or above, or at least about 15% of overall terpenes/terpenoids is still infused at about 60 minutes or above, or at least about 10% of the overall terpenes/terpenoids is still infused at about 90 minutes or above, following exposure to ambient air.

In an embodiment of the invention, the term "substantially" is interchangeable with the term "statistically substantially".

As used herein the term "paper products" encompasses various types of products made of paper. The paper product may present various colors and sizes. In one or more embodiments, the paper product is a smoking paper product. As used herein the term "smoking product" encompasses any optional product used for smoking and made of paper. In an embodiment of the invention, the smoking product is made of a paper for which the addition of an aroma and/flavor may be applicable. In an embodiment of the invention, the paper product is a smoking product. Suitable smoking products include, without limitation, a rolling paper, a tip, and a filter (e.g., a straw filter). Any smoking rolling paper, filters and tips are contemplated. Exemplary filters include those filters used in pipes or hookahs. In one or more embodiments, the term includes sanitary and/or toiletries paper products, such as toilet paper and pads. In one or more embodiments, the term does not include sanitary and/or toiletries paper products, such as toilet paper and pads.

In one or more embodiments, the paper product has a thickness of at least about 15 μπι. For example, the thickness may be no more than about 35 μπι, 30 μπι, 25 μπι or 20 μπι, or within the range of about 15 μπι to about 35 μιη, between about 15 μπι to about 30 μιη, or between about 18 μπι to about 22 μηι, or any value in between. Each possibility presents a separate embodiment of the invention.

In one or more embodiments, the paper product has a grammage (i.e., mass per unit of area) of at least about 10 g/m². For example, the grammage may be no more than about 20 g/m², 18 g/m², 17 g/m², 16 g/m² or 15 g/m², or within the range of about 10 g/m² to about 20 g/m², between about 10 g/m² to about 16 g/m², or between about 11 g/m² to 15 g/m², or any value in between. Each possibility presents a separate embodiment of the invention.

In one or more embodiments, the paper product has a density of at least about 350 kg/m³. For example, at least about 400 kg/m³, or at least about 500 kg/m³, or at least about 600 kg/m³, or any value in between. Each possibility presents a separate embodiment of the invention.

For example, the density may be no more than about 750 kg/m³, 700 kg/m³, 680 kg/m³, or 670 kg/m³, or within the range of about 400 kg/m³ to about 700 kg/m³, between about 630 kg/m³ to about 670 kg/m³, or any value in between. Each possibility presents a separate embodiment of the invention.

In an exemplary embodiment, the smoking paper may be porous, presenting pores with a diameter in the range of between about lxlO^"3 μπι to about 2xl0^"3 μπι. For example, about

1.4xl0^"3 μπι ιο about 1.6χ10^"3 μπι.

In an exemplary embodiment, the smoking paper may have porosity (herein referred to as percentage of the bulk volume of air) in the range of between about 50% to about 70%. For example, about 50% to about 65%, or about 54% to about 58%.

In an exemplary embodiment, the smoking paper may have smoothness (according to Bekk method) in the range of between about 10s to about 20s. For example, about 13 to about 20s.

As used herein the term "aroma compound" encompasses any compound that may add an aroma or odor to paper products. The aroma compound should be suitable such that it can be incorporated within a paper.

As used herein the term "flavor compound" encompasses any compound that may add flavor or taste to paper products. The flavor compound should be suitable such that it can be incorporated within a paper.

In one or more embodiment, the aroma and/or flavor compound is purified from a plant (e.g., from a plant extract). In one or more embodiment, the aroma and/or flavor compound is provided within a plant extract. In one or more embodiment, the aroma and/or flavor compound is a synthetic compound. In one or more embodiment, the aroma and/or flavor compound is a terpene. In one or more embodiment, the aroma and/or flavor compound is a terpenoid. In yet a further aspect of the invention, there is provided a composition comprising at least one terpene and/or terpenoid. The composition may further comprise a fixative agent. The composition may further comprise an antioxidant agent.

As used herein the term "terpenes" encompasses a large and diverse class of organic compounds, produced by a variety of plants or animals. Terpenes confer a strong odor. Terpenes are also major constituents of cannabis plants (such as cannabis sativa), which contain at least 120 identified compounds. The difference between terpenes and terpenoids is that terpenes are hydrocarbons, whereas terpenoids are considered as modified terpenes that contain additional functional groups, or in which methyl groups have been moved or removed, or oxygen atoms added.

For example, myrcene (a hydrocarbon) is a terpene, and linalool (an alcohol) is a terpenoid.

Terpenoids are also known as isoprenoids. Cannabis essential oils contain mostly mono- and sesqui-teprenes/terpenoids. Monoterpenes (e.g. limonene) contain 10 carbon atoms, and sesquiterpenes (e.g. caryophyllene) contain 15 carbon atoms.

"Major terpenes/terpenoids" are referred to herein as those compounds present in Cannabis sativa L strain in relatively high concentration. Depending on the cannabis strain, their amount usually varies from a few percent to about 50% of the total weight of the cannabis essential oil.

"Minor terpenes/terpenoids" are referred to herein as those compounds present in Cannabis sativa L strain in relatively low concentration. Their amount in cannabis essential oils may vary from below detection limit, to fractions of a percent, to (seldom) a few weight percent in some strains.

In an embodiment of the invention, the present invention is not limited in scope to the particular type of terpene/ terpenoid. In one embodiment, the terpenes/terpenoids is Generally Regarded As Safe (GRAS), i.e., an FDA designation that a chemical or substance added to food is considered safe. In one or more embodiment, the terpene/terpenoid is regarded as a cannabis essential oil. In one or more embodiments, the terpene/terpenoid is other than those terpenes/terpenoids known to exhibit toxicity.

In one or more embodiments, the terpene/terpenoid is selected from a mono terpene, a bicyclic terpene, a sesquiterpene, a diterpene, a triterpene, a tetraterpene, or from a terpene alcohol, terpene aldehyde or terpene ketone.

In one or more embodiments, the terpene/terpenoid is selected from the group consisting of (+) fenchol, (E)-caryophyllene, (E)-epoxy-ocimene, (E)-nerolidol, 1-epi-cubenol, 7-epi-sesquithujene, 8-cineole, allo-aromadendrene, aromadendrene, bicyclogermacrene, bisabolene, borneol, camphene, camphor, caryophyllene oxide, cis-ocimene, coahuilensol, curcumene, delta-3-carene, endo-fenchol, elemene, geraniol, germacrene, guaiene, guaiol, gurjunene, humulene epoxide II, ipsdienol, isoborneol, limonene, d-limonene, dipentene, linalool, menthol, muurolene, myrcene, nerol, p-cymen-8-ol, p-cymene, sabinene, sabinene hydrate, selina-3,7(l l)-diene, selinene, sesquicineole, sesquiphellandrene, sesquithujene, spathulenol, terpinen-4-ol, terpinene, terpinolene, thujene, trans-caryophyllene, trans-ocimene, viridiflorol, ylangene, a-bergamotene, a-bisabolol, a- cadinene, a-pinene, β-pinene, a-cedrene, a-eudesmol, a-humulene, a-longipinene, a-phelladerene, pinene, a-pinene, a-terpinene, a-terpineol, a-terpinolene, β-caryophyllene, β-eudesmol, β- farnesene, β-phellandrene, β-pinene, β-selinene, and A3-carene, or any combination thereof.

In one or more embodiments, the terpene/terpenoid is a major terpene/terpenoid. In one or more embodiments, the major terpene/terpenoid is selected from the group consisting of: (E)- caryophyllene, limonene, linalool, myrcene, trans-caryophyllene, α-humulene, a-pinene, β- caryophyllene, β-pinene, and any combination thereof. In one or more embodiments, the terpene/terpenoid is a minor terpene/terpenoid. In one or more embodiments, the minor terpene/terpenoid is selected from the group consisting of: (+) fenchol, (E)-epoxy-ocimene, (E)- nerolidol, 1-epi-cubenol, 7-epi-sesqui thujene, 8-cineole, allo-aromadendrene, aromadendrene, bicyclogermacrene, bisabolene, borneol, camphene, camphor, caryophyllene oxide, cis-ocimene, coahuilensol, curcumene, delta-3-carene, endo-fenchol, elemene, geraniol, germacrene, guaiene, guaiol, gurjunene, humulene epoxide II, ipsdienol, isoborneol, menthol, muurolene, nerol, p- cymen-8-ol, p-cymene, sabinene, sabinene hydrate, selina-3,7(l l)-diene, selinene, sesquicineole, sesquiphellandrene, sesquithujene, spathulenol, terpinen-4-ol, terpinene, terpinolene, thujene, trans-ocimene, viridiflorol, ylangene, a-bergamotene, a-bisabolol, a-cadinene, a-cedrene, a- eudesmol, a-longipinene, a-phelladerene, a-terpinene, a-terpineol, a-terpinolene, β-eudesmol, β- farnesene, β-phellandrene, β-selinene, and A3-carene, or any combination thereof.

In one or more embodiment, the terpene and/or terpenoid is purified from a cannabis plant. In one or more embodiment, the terpene and/or terpenoid is a synthetic compound. In one or more embodiment, the aroma and/or flavor compound is a derivative or a homologue of a terpene or a terpenoid, or a compound mimicking terpene or terpenoid. In one or more embodiment, the terpene/terpenoid is in an isolated form. In one or more embodiment, the terpene/terpenoid is isolated from a cannabis or from any other plant or animal. As used herein, the term "isolated" refers to the terpene and/or terpenoid when separated from at least some of the components with which it is usually associated in nature or in in vitro conditions, and/or prepared or purified by a process that involves the hand of a man.

In one or more embodiment, the terpene/terpenoid is substantially free of any natural or synthetic compounds. In one or more embodiment, the terpene/terpenoid is essentially free of any natural or synthetic compounds. In one or more embodiment, the terpene/terpenoid is free of any natural or synthetic compounds.

As used here, the term "substantially free" refers to a compound or composition comprising less than about 0.5%, or less than about 0.4%, or less than about 0.3%, or less than about 0.2%, or less than about 0.1%, or any percentage in between of a particular compound.

As used herein, the term "essentially free" refers to a compound or composition comprising less than about 0.05%, or less than about 0.04%, or less than about 0.03%, or less than about 0.02%, or less than about 0.01%, or less than about 0.005%, or any percentage in between, or having only trace amounts of a particular compound or of other compounds.

As used herein the purified or isolated terpene and/or terpenoid, refers to the compound being substantially or essentially pure of any other naturally occurring or non-naturally occurring substances, including cannabinoids that occur naturally in cannabis plants. In this context "substantially pure" can be taken to mean that no cannabinoids other than terpenes and/or terpenoids are detectable by HPLC. According to some embodiments, the purified terpene and/or terpenoid comprises up to 1 % of non-terpene or terpenoid compound.

In one or more embodiments, the herein disclosed terpene/terpenoid composition or rolling paper comprising same includes a mixture of pure and synthetic terpene and/or terpenoid compounds. In one or more embodiments, the herein disclosed terpene/terpenoid composition or rolling paper comprising same includes a profile of terpenes and/or terpenoids compounds that is substantially similar to a cannabis plant.

In some embodiments, the terpene(s) and/or terpenoid(s) is present in the terpene/terpenoid composition at about 40% to about 60%, or at about 45% to about 55% by weight. For example, the terpene(s) and/or terpenoid(s) is present at about 49% to about 51% by weight. In some embodiments, the terpene(s) and/or terpenoid(s) weight per paper area is below about 1 mg/cm². In some embodiments, the terpene(s) and/or terpenoid(s) weight per paper area is at least about 0.2 mg/cm², 0.4 mg/cm², or 0.5 mg/cm². For example, the terpene(s) and/or terpenoid(s) weight per paper area is within the range of about 0.2 mg/cm² to about 0.8 mg/cm², or about 0.2 mg/cm² to about 0.7 mg/cm², or about 0.2 mg/cm² to about 0.5 mg/cm². In an exemplary embodiment, the terpene(s) and/or terpenoid(s) weight per paper area is about 0.37 mg/cm².

In one or more embodiments, the aroma and/or flavor compound presents a chemical profile or composition that is substantially similar to the chemical composition of those compounds present naturally within a cannabis plant. Said similarity can be of a full profile or a partial profile consisting of at least two terpenes and/or at least two terpenoids. In an exemplary embodiment, when a combination of at least two terpenes and/or at least two terpenoids is provided, the weight or molar ratio between the at least two terpenes and/or the at least two terpenoids is substantially similar to the actual ratio between those compounds present in the natural cannabis plant.

In one or more embodiments, the smoking product of the invention includes at least one type of terpene. For example, the smoking product includes a mixture (or a profile) comprising at least 2 types of terpenes, or at least 4, 6, 8, 10, 12, 14, 16, 18, 20, 22, 24, 26, 28 or 30 types of terpenes, or any value in between. Each possibility presents a separate embodiment of the invention.

In one or more embodiments, the smoking product of the invention includes at least one type of terpenoid. For example, the smoking product includes a mixture (of a profile) comprising at least 2 types of terpenoids, or at least 4, 6, 8, 10, 12, 14, 16, 18, 20, 22, 24, 26, 28 or 30 types of terpenoids. Each possibility presents a separate embodiment of the invention.

In one or more embodiments, the aroma and/or flavor compound(s) is incorporated within the paper, infused within the paper, bound within the paper, and/or coated onto the paper.

In one or more embodiments, the herein disclosed composition or products comprising same further contain a fixating agent (interchangeable with the term "fixative agent").

Terpenes and terpenoids are known in their relatively high volatile characteristics. Accordingly, in typical cases, providing paper products with terpenes or terpenoids will result in fast evaporation of the terpenes/terpenoids from the paper. The present invention overcomes this obstacle by adding an agent (hereinafter referred to as "a fixative agent") that affords stability and enhances retention of the terpene/terpenoid within the paper product. Further advantageously, the terpenes and/or terpenoids are maintained within the paper even in an opened environment (i.e., ambient air) and even when the product is being smoked.

The "fixative agent" may be any agent capable of incorporating or binding or maintaining, or stabilizing, or enhance retention, and/or reduce evaporation of the flavor and/or aroma compound within the paper. In one or more embodiments, the fixative agent is capable of binding to oils. In one or more embodiments, the fixative agent is soluble in oil (i.e., it is oil soluble). In one or more embodiments, the fixative agent is not water soluble, or in other words is water insoluble. In one or more embodiments, the fixative agent is amphiphilic.

As used herein the term "oil soluble" refers to a compound which is soluble in nonpolar substances, such as ether, chloroform, and oils. Oil-soluble compounds are often insoluble in water.

In one or more embodiments, the fixative agent is capable of binding to volatile oils. In one or more embodiments, the fixative agent is capable of binding to aroma oil, or essential oil. In one or more embodiments, the fixative agent is capable of binding to a terpene and/or terpenoid.

The fixative may thus have binding affinity to terpene and/or terpenoid. The fixative agent may bind to a terpene and/or terpenoid via a chemical bond selected from an ionic bond, a polar bond, a covalent bond, and/or a hydrogen bond. In one or more embodiments, the fixative agent may bind to a terpene and/or terpenoid via a polar bond, or a hydrogen bond.

In one or more embodiments, the fixative agent is capable of binding (to a paper, or to one or more substances within a paper (e.g., cellulose). The fixative may thus have binding affinity to cellulose. The fixative agent may bind to cellulose via a chemical bond such as via an ionic bond, via a polar bond, via a covalent bond, and/or via a hydrogen bond. Each possibility presents a separate embodiment of the invention. For example, it can interact with terpene and/or terpenoid via van der Waals forces.

In one or more embodiments, the fixative agent is capable of binding concomitantly to a terpene and/or terpenoid and to cellulose.

In one or more embodiments, the fixative agent is a fragrance fixative. As used herein "fragrance fixatives" are liquid or waxy, natural or synthetic compounds with low to no volatility that can dissolve fragrant compounds (e.g., terpenes/terpenoids). The fixative agent is used herein and is capable of substantially reducing the evaporation of one or more terpene/terpenoid from the paper product. In an embodiment of the invention, the fixatives are non-toxic or possess a very low toxicity and, when burned, produce low/insignificant amounts of irritating/toxic/obnoxious decomposition products. In an embodiment of the invention, the fixatives have a very weak to no smell. In an embodiment of the invention, the fixatives do not affect substantially the smell of the terpene composition. In one or more embodiments, the fixative is flavorless. In one or more embodiments, the fixative is odorless. In an embodiment of the invention, the fixative is a polymer (e.g., a polypropylene glycol-based polymer). For example, the polypropylene glycol is having a M.W. (Molecular Weight) of 160 Dalton to 10000 Dalton. In an exemplary embodiment, the molecular weight should be within the ranges of 160-400 Da, or 4000-10000 Da. Such compounds with these molecular weights have the lowest toxicity. In one exemplary embodiment, the fixative is PPG-20 Methyl Glucose Ether (a.k.a, Glucam P-20). In a further exemplary embodiment, the fixative is 1,3- butanedeiol. In a further exemplary embodiment, the fixative is triethyl citrate.

In some embodiments, fixative is present in the terpene/terpenoid composition at about 30% to about 70% by weight. For example, the fixative is present in the terpene/terpenoid composition at about 40% to about 70%, or at about 45% to about 60%, or at about 45% to about 55%, or at about 49% to about 51% by weight. In one or more embodiments, the weight ratio between the fixative agent and the terpene and/or terpenoid is about 5: 1 to about 1 :5, or about 3: 1 to about 1:3, or about 1 : 1. In one or more embodiments, the weight ratio between the fixative agent and the terpene and/or terpenoid is about 5: 1 to about 1:5, or about 3: 1 to about 1:3, or about 1 : 1.

In some embodiments, the fixative agent weight per paper area is below about 1 mg/cm². In some embodiments, the fixative weight per paper area is at least about 0.2 mg/cm², 0.4 mg/cm², or 0.5 mg/cm², or 1 mg/cm². For example, the fixative weight per paper area is within the range of about 0.2 mg/cm² to about 0.8 mg/cm², or about 0.2 mg/cm² to about 0.7 mg/cm², or about 0.2 mg/cm² to about 0.5 mg/cm². In an exemplary embodiment, the fixative weight per paper area is about 0.37 mg/cm². In one or more embodiments, the fixative agent is glucam.

In one or more embodiments, the fixative does not dissolve or solubilize the main paper compound cellulose. Accordingly, the fixative should possess δΡ and δΗ below the δΡ and δΗ of cellulose. A suitable fixative is further expected to possess δΡ and δΗ above the δΡ and δΗ of terpenes and terpenoids in order to allow solubilizing the terpenes and terpenoids.

Thus, in one or more embodiments, the fixative agent has δΡ value of below about 19.9 MPa½. For example, the fixative agent possesses a δΡ value of below 19, or below 18, or below 17 MPa½. For example, depending on the terpenes/terpenoids used, the fixative agent possesses a δΡ value of above about 1, or above 2, or above 3, or above 4, or above 5 and below 19.9 MPa½.

Thus, in one or more embodiments, the fixative agent has δΗ value of below about 22.5 MPa½.

For example, the fixative agent possesses a δΗ value of below 22, or below 21, or below 20 MPa½. For example, depending on the terpenes/terpenoids used, the fixative agent possesses a δΗ value of above 2, or above 3, or above 4, or above 5, or above 6, or above 7 and below about 22.5 MPa½.

In some embodiments, the terpene/terpenoid composition or paper product comprising same further comprises an antioxidant. The antioxidant prevents oxidation of the terpenes and terpenoids, allowing an enhanced stability and/retention of the paper product. The antioxidant in the presently described compositions and/or products can include any known acceptable compound that functions by inhibiting oxidation.

As used herein, the term "antioxidant agent" refers to compounds being either natural or synthetic that possess the capacity to slow down or prevent the oxidation/decomposition of an extremely wide range of products (e.g., foods, fragrances to plastics). Some antioxidants are better soluble in water; other antioxidants are better soluble in oils. In an exemplary embodiment of the invention, the antioxidant is oil soluble. In one or more embodiments, the antioxidant dissolves in the herein disclosed composition of terpene/terpenoid.

In one or more embodiments, the antioxidant is not water soluble, or in other words is water insoluble. Alternatively, or additionally, the antioxidant is amphiphilic.

In one or more embodiments, the antioxidant is capable of binding to volatile oils. In one or more embodiments, the antioxidant is capable of binding to aroma oil, or essential oil. In one or more embodiments, the antioxidant is capable of binding to a terpene and/or terpenoid. The antioxidant may thus have binding affinity to terpene and/or terpenoid. The antioxidant may bind to a terpene and/or terpenoid via a chemical bond such as via an ionic bond, via a polar bond, a covalent bond, and/or a hydrogen bond. For example, it can interact with terpene and/or terpenoid via van der Waals forces.

In one or more embodiments, the antioxidant is a fragrance antioxidant.

In one or more embodiments, the antioxidant is capable of binding to a paper, or to one or more substances within a paper, (e.g., cellulose). The antioxidant may thus have binding affinity to cellulose.

As used herein "fragrance antioxidant" can dissolve fragrant compounds (e.g., terpenes/terpenoids). The antioxidant is used herein and is capable of substantially preventing oxidation of one or more terpene/terpenoid, thereby contributing in enhancing the stability and/or retention of the terpenes and terpenoids in the paper product. In an embodiment of the invention, the antioxidant is non-toxic or possesses a very low toxicity and, when burned, produce low/insignificant amounts of irritating/toxic/obnoxious decomposition products. In an embodiment of the invention, the antioxidant has a very weak to no smell. In an embodiment of the invention, the antioxidant does not affect substantially the smell of the terpene and/or terpenoid composition. In one or more embodiments, the antioxidant is flavorless. In one or more embodiments, the antioxidant is odorless.

In an embodiment of the invention, the antioxidant is selected from butylated hydroxyanisole (BHA, E320), butylated hydroxytoluene (BHT, E321), cannabidiol (CBD), propyl gallate (PG, E310), tertiary butylhydroquinone (TBHQ, E319), tocopherols (Vitamin E, E306-E309), vitamin C, vitamin E, and any combination thereof.

The antioxidant may be used in various concentrations and the optimal concentration depends on the type of the antioxidant used. The choice of antioxidant, its concentration, or the use of mixes of more than one antioxidant should comply with the respective regulations.

For example, BHA is used to preserve essential oils in concentrations of up to 0.5%. Natural cannabidiol is as good as synthetic BHT and can be used in concentrations of less than 0.5%.

In some embodiments, the antioxidant is present in the terpene/terpenoid composition at about

0.1% to about 5% by weight. For example, the antioxidant is present at about 0.1% to about 2%, or at about 0.5% to about 2% by weight. In some embodiments, the antioxidant is present at about 0.9% to about 1%, or at about 0.93% to about 0.95% by weight of the terpene/terpenoid composition.

In an exemplary embodiment of the invention, the antioxidant is tocopherol or a derivative thereof. In a further embodiment of the invention, the antioxidant is vitamin E, or a derivative thereof.

In some embodiments, vitamin E is present in the composition at about 0.5% to about 2.5% by weight of the composition. For example, vitamin E is present at about 0.5% to about 2% by weight, or at about 0.75% to about 1.5%. In some embodiments, vitamin E is present at about 1% by weight.

In some embodiments, antioxidant weight per paper area is below about 0.1 mg/cm², or below about 0.01 mg/cm². For example, the antioxidant weight per paper area is about 7xl0^"3 mg/cm²

In some embodiments, a terpene/terpenoid composition provided herein is substantially antioxidant free. In some embodiments, a terpene/terpenoid composition provided herein is essentially antioxidant free. In some embodiments, a terpene/terpenoid composition provided herein is antioxidant free. As used here, the term "substantially free" refers to a compound or composition comprising less than about 0.5%, or less than about 0.4%, or less than about 0.3%, or less than about 0.2%, or less than about 0.1%, or any percentage in between of a particular compound.

The invention overcomes the obstacle associated with evaporation of many flavor and/or aroma compounds by incorporation of one or more fixative agent and/or one or more antioxidant agent, and/or by applying pressure when manufacturing the paper product.

In one or more embodiments, the herein disclosed paper product does not include aroma and/or favor compound other than terpene and/or terpenoid. In one or more embodiments, the herein disclosed paper product consists of at least one compound selected from the lists of: terpene(s), terpenoid(s), fixative agent(s), and antioxidant(s).

As used herein, the phrase "effective amount" describes an amount of the aroma and/or flavor compound that is sufficient to provide an added aroma and/or flavor to the paper product.

In a further aspect, the present invention provides a method of manufacturing an aromatized and/or flavored paper product. The herein disclosed paper products are prepared using the following steps. Preparing a composition comprising certain amounts of an aroma and/or a flavor compound.

Optionally, the composition includes at least one antioxidant and/or at least one fixative agent.

Applying an amount of the composition on one side of the paper. Spreading the composition, optionally with a cotton pad or using one or more rollers. Alternatively, or additionally the paper product may be immersed within a bath containing the terpene and/or terpenoid composition. Optionally, an excess amount of the composition is being removed. Optionally, applying an amount of the composition on the other side of the paper, and spreading the composition, optionally with a cotton pad or using one or more rollers. Optionally, inserting the composition by physical means, such as by applying pressure, to thereby press and insert the compounds within the composition into the pores and fibers of the paper.

In an embodiment of the invention, the pressure is between about lOOg/sq inch and about 5000g/sq inch. For example, between about lOOg/sq inch and about 4000g/sq inch, between about lOOg/sq inch and about 3000g/sq inch, between about lOOg/sq inch and about 2000g/sq, between about lOOg/sq inch and about lOOOg/sq inch, between about lOOg/sq inch and about 500g/sq inch, between about 400g/sq inch and about 5000g/sq inch, between about 800g/sq inch and about 5000g/sq inch, between about lOOOg/sq inch and about 5000g/sq, between about 2000g/sq inch and about 5000g/sq inch, between about 3000g/sq inch and about 5000g/sq inch, or between about 4000g/sq inch and about 5000g/sq, or any value in between.

For example, pressure may be applied for each side of the paper or for both sides concomitantly at least one time, at least two times, at least three time, or at least four time.

The method may optionally include cutting the paper to any desired dimensions and packing the paper with the aroma and flavor compounds inserted therein the paper.

In one or more embodiments, the method further comprises a step of sealing the package.

In one or more embodiments, the paper is inserted within the package immediately thereafter the paper is prepared.

Optionally, the paper is being coated (e.g., by spraying) with cellulose to seal the surface. Additional pressure may optionally be applied also following the cellulose coating.

The method may optionally include a step of incubating the paper product with the composition for at least about 10 minutes.

Reference to the term "about" has its usual meaning in context to the herein invention of a reasonable variation from a stated amount that retains the ability to achieve one or more functional effect to substantially the same extent as the stated amount. The term may also refer herein to a value of plus or minus 15% of the stated value; plus or minus 10% of the stated value; or plus or minus 5%, or plus or minus 1%, or plus or minus 0.5%, or plus or minus 0.1%, or any percentage in between. For example, "about 20" may mean or include amounts from 18 up to and including 22, to the extent those amounts achieve one or more functional effect to substantially the same extent as an amount of 20 would.

EXAMPLES

The invention will be described in greater detail by way of specific examples. The following examples are offered for illustrative purposes, and to exemplify the compositions and methods described herein and are not intended to limit the invention in any manner. Many variations will suggest themselves and are within the full intended scope. Those of skill in the art will readily recognize a variety of non-critical parameters which can be changed or modified to yield essentially the same results.

Example 1

In order to maintain the fragrance in the paper, the fixative agent should dissolve the highly hydrophobic terpene mixture and, at the same time, possess a good adhesion to the hydrophilic cellulose fibers of the paper. Potential fixatives were evaluated using the Hansen Solubility Parameters (HSP; Hansen solubility parameters: a user's handbook. 2nd ed., edited by Charles Hansen, CRC Press, 2007, ISBN 0-8493-7248-8). HSP affords for a good estimate of: i) Van der Waals forces between the molecules (i.e., 5D); ii) attraction due to polar interactions (i.e., 5P); and iii) forces due to hydrogen bonds (i.e., δΗ). The HSP values of cellulose, some fixatives, and exemplary cannabis fragrance terpenes are presented at Table 1. The table shows that cellulose has very high δΡ and δΗ values, compared to terpenes. A good fixative is expected to possess δΡ and δΗ below 19.9 and 22.5, respectively in order to avoid from dissolving the main paper product cellulose. A good fixative is further expected to possess δΡ and δΗ above the δΡ and δΗ of terpenes and terpenoids in order to allow dissolving the terpenes and terpenoids.

Table 1. Hansen Solubility Parameters (HSP) of cellulose, fixatives, and major cannabis fragrance terpenes.

*The HSP of PPG-20 Methyl Glucose Ether are unknown but they are expected to be between the HSP of the shortest and most polar polypropylene glycol, dipropylene glycol, and the HSP of high molecular weight polypropylene glycols that are less polar. Example 2

Aim:

Determination of the aroma stability of: i) pure terpene profile and ii) a mixture of a pure terpene profile in combination with a fixative agent, and an antioxidant agent.

Method:

Three sets of rolling papers (2 consisting of 6 papers each and 1 of 2 papers) were weighed before and after applying the terpene mixtures thereon. The papers were then individually closed and incubated in centrifuged tubes for 1 hour. The weight of each paper was thereafter measured at time 0 (immediately after taking it out of the tube), 3, 10, 20, 40, 60 and 90 minutes while staying in an opened environment.

1. The first set of 6 papers - pure terpene profile (28 μΐ) was applied on both sides of the paper (14 μΐ on each side) by an 8-channel pipette, and the liquid was distributed by a roller.

2. The set of 2 papers - pure terpene profile (14 μΐ) was applied on only one side of the paper by an 8-channel pipette, and the liquid was distributed by a roller.

3. The second set of 6 papers - a mixture of pure terpene profile and a fixative agent, and antioxidative agent was applied on both sides of the paper (14 μΐ on each side) by an 8- channel pipette, and the liquid was distributed by a roller. Results:

As can be seen in FIG. 1 , a combination of a mixture of pure terpene profile, a fixative agent, and an antioxidative agent (striped line) achieves a stable product, wherein the terpene composition is significantly maintained within the paper even following 90 minutes. A composition comprising terpenes only in a similar amount (dotted line) was significantly less stable. A composition comprising terpenes in lowest amount presented steeper evaporation of the terpenes (a full line). The increase in weigh % show in all cases following 60 minutes is due to a certain level of water adsorption. Example 3

Paper samples were infused with a terpene and/or terpenoid composition (hereinafter "composition 1") and with a comparable composition that further comprises a fixative agent, i.e., PPG-20 Methyl Glucose Ether (i.e., Glucam P-20) at an amount of about 50% by weigh and an antioxidant, i.e., vitamin E at an amount of 0.95% by weight acetate (hereinafter "composition 2").

Paper samples were maintained in closed chamber until evaluation. The samples were then dissolved in chloroform to obtain solutions with total terpenes and terpenoids concentration of 125 mg/ml. A volume of 26.7 μΐ (contains 3.34 mg of the sample) was injected into a GC/MS. The GC/MS equipment is Agilent Technologies, consisting of GC System 7890A, injector with autosampler 7683B Series, and EI/CI MSD with Triple-Axis Detector 5975C. Gas: Helium 5.0; pressure 6.9972 psi. Column: HP-5MS 5% Phenyl Methyl Silox, temperature limit from -60 °C to 325 °C; length: 30 m, diameter: 0.25 mm, film: 0.25 μπι. Temperature program: 40 °C for 3 min, then 5 °C/min to 300 °C for 5 min. Run time: 60 minutes. Split Ratio: 15: 1. Split Flow: 29.9 ml/min. MS source: 230 °C, max 250 °C; MS Quad.: 150 °C, max 200 °C.

Table 2 presents the percentage of each particular terpene/terpenoid compound, in each sample tested relative to the total terpene and terpenoid content as measured at unexposed (to air) conditions.

Table 2- percentage of each terpene compound and Vitamin E in the tested paper samples

Peak R.T.[min] Compound % of total

Composition 1 Composition 2

1 9.52 a-Pinene 0.78 0.68

2 10.05 Camphene 0.08 n.d.

3 10.83 Sabinene 0.08 n.d.

4 10.98 β-Pinene 0.91 0.80

5 11.41 β-Myrcene 1.10 0.97

6 12.28 a-Terpinene 1.13 0.95

7 12.62 7-Cymene 0.73 2.14

8 12.73 Limonene + eucalyptol 5.25 4.12

9 13.03 c .v-Ocimene 9.40 10.73

10 13.08 trans-Ocimene 2.68 n.d.

11 13.90 γ-Terpinene 34.67 35.21

12 14.82 Terpinolene 34.62 36.68

13 14.89 Dehydro-j?-cymene 1.12 tr.

14 15.01 β-Linalool 0.12 0.08

15 15.64 Fenchol, exo- 0.52 0.46

16 16.95 Isoborneol 0.08 n.d.

17 17.21 Borneol 0.07 n.d.

18 17.33 ira/is-2-Caren-4-ol 0.1 1 0.05

19 17.68 / Cymen-8-ol 0.06 n.d.

20 17.89 /?-Menth-l-en-8-ol 0.25 0.22

21 20.36 Bornyl acetate 0.05 n.d.

22 24.06 β-Caryophyllene 2.54 2.22

23 24.76 Humulen 0.08 n.d.

24 24.94 a-Caryophyllene 0.87 0.04

25 25.83 Eremophylene 0.08 tr.

26 28.01 Caryophyllene oxide 0.09 0.05

27 54.73 Vitamin E acetate tr. 2.90

*n.d. designates: not detected; tr. designates: trace amount (below 0.01% of the total).

Table 2 shows the terpenes and terpenoids profile in composition 1 and composition 2, in unexposed (to air) conditions. The terpene/terpenoid profile in each of the 1 and 2 compositions was also evaluated at time points 0, 10, 20, and 30 min after unpacking the samples. Table 3 - percentage of each particular terpene/terpenoid compound, in composition 1 relative to the total soluble compounds in the final product at various time points (stability of raw material over time).

Peak R.T. Compound % of composition 1

[min]

0 min 10 min 20 min 30 min

1 13.68 γ-Terpinene Tr. 5.15 2.70 6.10

2 14.54 Terpinolene 12.04 Tr. 3.32 9.18

3 14.69 Dehydro-j?-cymene Tr. Tr. Tr. 0.85

4 15.01 β-Linalool Tr. Tr. Tr. 1.01

5 15.64 exo-Fenchol Tr. Tr. 1.76 4.09

6 16.97 Borneol Tr. Tr. Tr. 0.72

7 17.35 trans -2-Caren-4-o\ Tr. Tr. 1.64 2.48

8 17.70 j?-Cymene-8-ol Tr. Tr. 1.91 2.03

9 17.91 j?-Menth-l-en-8-ol Tr. Tr. 1.76 2.89

10 24.03 β-Caryophyllene 10.71 5.48 2.20 4.36

11 24.93 a-Caryophyllene Tr. 2.10 0.85 1.81

12 54.70 Vitamin E acetate Tr. 3.20 10.35 1.84

Figure 2 and the above table 3 present % of each terpenoid present in paper products that were incorporated with composition 1 at various time intervals after opening the packages.

The data shows that terpene/terpenoid profile at time point 0 is completely different then the terpene/terpenoid profile at the other time points tested. Namely, the profile of the terpene and terpenoid molecules changes over time. That is due to the fact that certain terpenes/terpenoids may evaporate faster than other terpenes/terpenoids. Consequently, the ratio between the terpenes/terpenoids changes hence the terpenes/terpenoids molecular profile. The terpene/terpenoid profile has a significant effect on taste. When the ratio of the terpene/terpenoid compound changes, the overall flavor and aroma changes.

- percentage of particular terpene/terpenoid compound, in composition 2 relative to the total soluble compounds content in sample at various time points.

Peak R.T. [min] Compound % of composition 2

0 min 10 min 20 min 30 min

1 12.62 j?-Cymene 0.39 0.28 Tr. 0.76

2 12.97 β-irans-Ocymene 1.24 0.90 0.58 1.27

3 13.68 γ-Terpinene 10.78 7.91 5.21 10.18

4 14.54 Terpinolene 17.01 11.90 7.83 15.26

5 14.69 Dehydro-j?-cymene 1.80 1.26 0.70 1.36

6 15.01 β-Linalool 1.27 0.83 0.57 0.68

7 15.64 exo-Fenchol 4.66 3.20 2.40 3.32

8 16.97 Iso-Borneol 1.06 0.65 Tr. 0.38

9 17.24 Borneol n.d. 0.71 0.48 0.45

10 17.35 trans -2-Caren-4-o\ 1.39 1.08 0.82 1.44

11 17.70 j?-Cymene-8-ol 1.50 1.25 1.05 1.18

12 17.91 j?-Menth-l-en-8-ol 3.47 2.50 1.64 1.69

13 18.03 γ-Terpineol 0.43 0.31 Tr. 0.21

14 24.03 β-Caryophyllene 8.81 5.36 3.31 4.01

15 24.93 a-Caryophyllene 3.68 2.28 1.40 1.62

16 25.83 Eremophylene 0.46 0.33 Tr. 0.34

17 28.01 Caryophylene oxide 0.92 0.67 0.50 0.48

18 54.70 Vitamin E acetate 5.59 4.93 5.18 3.07

Figure 3 and the above table 4 present the % of each terpenoid present in paper products that were incorporated with composition 2 at various time points after opening the packages. The data shows that terpene/terpenoid profile (i.e., molecule type and/or ratio of the compounds within the composition) is stably maintained at all time points tested following exposure to ambient environment. Consequently, the overall flavor and aroma should be maintained over time.

Although the invention has been described in conjunction with specific embodiments thereof, it is evident that many alternatives, modifications, and variations will be apparent to those skilled in the art. Accordingly, it is intended to embrace all such alternatives, modifications, and variations that fall within the spirit and broad scope of the appended claims.

Claims

1. An aromatized and/or flavored paper product, the paper product comprising, one or more terpene(s) and/or one or more terpenoid(s), and at least one of a fixative agent and an antioxidant.

2. The paper product of claim 1, wherein the terpene and/or terpenoid is maintained in the paper product for a substantially longer time as compared to a paper product without a fixative agent and an antioxidant.

3. The paper product of claim 1 or 2, wherein the antioxidant is selected from the group consisting of: butylated hydroxyanisole, butylated hydroxytoluene, cannabidiol, propyl gallate, tertiary butylhydroquinone, tocopherol, vitamin E, and any combination thereof.

4. The paper product of any one of claims 1-3, wherein the fixative agent is characterized by at least one of: oil solubility, binding capacity to cellulose, biding capacity to terpene and/or terpenoid, non-toxicity, flavorless, odorless, or any combination thereof.

5. The paper product of any one of claim 1-4, wherein the fixative agent is selected from the group consisting of: a polypropylene glycol, a PPG-20 Methyl Glucose Ether, 1,3-butanedeiol, triethyl citrate, and any combination thereof.

6. The paper product of claim 5, wherein the polypropylene glycol is having a M.W. of about 160 Da to about 10,000 Da.

7. The paper product of claim 5, wherein the polypropylene glycol is having a M.W. selected from about 160 Da to about 400, and about 4,000 to about 10,000 Da.

8. The paper product of any one of claims 1-7, wherein the terpene and/or the terpenoid is provided as a natural cannabis plant extract.

9. The paper product of any one of claims 1-8, wherein the terpene and/or the terpenoid is an isolated terpene and/or the terpenoid.

10. The paper product of any one of claims 1-9, wherein the terpene and/or the terpenoid is a synthetic compound.

11. The paper product of any one of claims 1-10, wherein the paper product is a smoking paper product.

12. The paper product of claim 11 , wherein the smoking paper product is selected from a rolling paper, a tip and a filter.

13. The paper product of any one of claims 1-12, wherein the paper is porous presenting pores having a diameter of about lxlO^"3 μπι to about 2x10^~3 μπι.

14. The paper product of any one of claims 1-13, wherein said paper product is manufactured by applying onto said paper a composition comprising one or more terpene(s) and/or one or more terpenoid(s), and at least one of a fixative agent and an antioxidant.

15. The paper product of claim 14, wherein the one or more terpene(s) and/or one or more terpenoid(s) is present within said composition in an amount of about 45% to about 55%, by weight of the composition.

16. The paper product of claim 14 or 15, wherein the antioxidant is present within said composition in an amount of about 0.1 % to about 2% by weight of the composition.

17. The paper product of any one of claims 14-16, wherein the fixative agent is present within said composition in an amount of about 45% to about 55% by weight of the composition.

18. The paper product of any one of claims 14-17, wherein the weight ratio between the fixative agent and the terpene and/or terpenoid is about 3: 1 to about 1:3.

19. The paper product of claim 18, wherein said ratio is about 1: 1.

20. The paper product of anyone of claims 1-19, wherein evaporation of the terpene and/or terpenoid is substantially reduced as compared to a comparable paper product without a fixative agent and an antioxidant.

21. The paper product of anyone of claims 1-19, wherein the overall amount of the terpene and/or terpenoid remains bound to the paper for at least about 10 minutes following exposure of the paper to ambient environment.

22. The paper product of any one of claims 1-21, comprising a terpene and/or terpenoid profile presenting substantial similarity to the terpene and/or terpenoid profile present naturally within a cannabis strain.

23. The paper product of claims 22, wherein said profile is stably maintained for at least about 10 minutes at ambient environment.

24. The paper product of claim 22 or 23, wherein at least about 50% of the terpenes/terpenoids molecule types remain in the paper product, following 5 minutes exposure to ambient air.

25. The paper product of any one of claims 1-23, further comprising a cellulose coat provided on top of said paper product.

26. The paper product of any one of claims 14-25, being manufactured by applying pressure onto said paper following, or concomitantly to applying said terpenes/terpenoids composition.

27. The paper product of claim 26, wherein said pressure is about lOOg/sq inch to about 5000g/sq.

28. The paper product of any one of claims 1-27, wherein the terpene(s) and/or terpenoid(s) is present in the paper product in an amount of about 0.2 mg/cm² to about 1 mg/cm².

29. The paper product of any one of claims 1-28, wherein the terpene(s) and/or terpenoid(s) is present in the paper product in an amount of about 0.2 mg/cm² to about 1 mg/cm².

30. The paper product of any one of claims 1-29, wherein the fixative agent is present in the paper product in an amount of about 0.2 mg/cm² to about 1 mg/cm².

31. A method of producing an aromatized and/or flavored paper product, the method comprising preparing a composition comprising one or more terpene(s) and/or one or more terpenoid(s); applying the composition onto the paper product;

applying pressure onto the paper product; and

removing excess of said composition from said paper product; thereby manufacturing an aromatized and/or flavored paper product.

32. The method of claim 31, wherein said composition further comprises at least one of a fixative agent and an antioxidant.

33. The method of claim 31 or 32, further comprising applying a cellulose layer over said paper product after removing excess of said terpene(s) and/or terpenoid(s) composition.

34. The method of any one of claims 31-33, further comprising packing said paper product within a hermetically sealed package.

35. The method of any one of claims 31-34, wherein said applying pressure is conducted using a roller and wherein said pressure is within the range of about lOOg/sq inch to about 5000g/sq inch.

36. The method of any one of claims 31-35, wherein said paper product is a smoking paper product.

37. The method of claim 36, wherein the smoking paper product is selected from a rolling paper, a tip and a filter.

38. The method of claim 37, wherein the smoking paper product is a rolling paper and wherein applying the composition onto the paper product is conducted on both sides of the rolling paper.