US20100063011A1 - Organic compounds - Google Patents

Organic compounds Download PDF

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Publication number
US20100063011A1
US20100063011A1 US12/066,518 US6651806A US2010063011A1 US 20100063011 A1 US20100063011 A1 US 20100063011A1 US 6651806 A US6651806 A US 6651806A US 2010063011 A1 US2010063011 A1 US 2010063011A1
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US
United States
Prior art keywords
methyl
actives
formula
compounds
skin care
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US12/066,518
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English (en)
Inventor
Andreas Natsch
Michael Wasescha
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Givaudan SA
Original Assignee
Givaudan SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Givaudan SA filed Critical Givaudan SA
Assigned to GIVAUDAN SA reassignment GIVAUDAN SA ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: NATSCH, ANDREAS
Publication of US20100063011A1 publication Critical patent/US20100063011A1/en
Abandoned legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/74—Biological properties of particular ingredients
    • A61K2800/75—Anti-irritant
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/05—Phenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/275—Nitriles; Isonitriles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/347—Phenols

Definitions

  • the present invention relates to organic compounds having the ability to reduce or suppress the formation of skin irritation induced by extraneous causes, and to compositions comprising them for topical application to the skin. It further relates to a method of reducing or suppressing the onset of skin irritation by extraneous causes.
  • the human skin is constantly exposed to environmental stresses, such as heat and cold, air pollution, exceptionally dry air or exaggerated UV irradiation.
  • a further form of stress can come from the application of cosmetic products or personal wash products.
  • certain soap acids and some surfactants, in particular anionic and cationic surfactants are known to stress the skin.
  • Antiperspirant salts such as aluminum salts and zirconium salts contained in antiperspirant products, retinol and derivatives thereof contained in anti-aging products, ⁇ -hydroxy acids such as glycolic acid or lactic acid contained in anti-wrinkle products are also known to stress the skin.
  • prostaglandins are mediators being formed upon a wide variety of different forms of external stress applied to the human skin, which may become apparent in redness of the skin, particularly on normal, healthy skin.
  • topical application compositions such as cosmetic products and personal wash products, which suppress or reduce the formation of prostaglandins, in particular prostaglandin E 2 (PGE 2 ).
  • fragrance ingredients have the ability to reduce or suppress the formation of prostaglandins in skin cells.
  • the present invention refers in one aspect to the use of a compound for the preparation of topical skin care compositions for reduction of skin irritation, wherein the compound is selected from the list consisting of
  • the actives for reducing skin irritation as hereinabove described may be combined with all known odorant molecules selected from the extensive range of natural products and synthetic molecules currently available, such as essential oils, alcohols, aldehydes and ketones, ethers and acetals, esters and lactones, macrocycles and heterocycles, and/or in admixture with one or more ingredients or excipients conventionally used in conjunction with odorants in fragrance compositions, for example, carrier materials, and other auxiliary agents commonly used in the art.
  • ingredients are, for example, described in “Perfume and Flavor Materials of Natural Origin”, S. Arctander, Ed., Elizabeth, N.J., 1960; “Perfume and Flavor Chemicals”, S. Arctander, Ed., Vol. I & II, Allured Publishing Corporation, Carol Stream, USA, 1994; and “International cosmetic ingredient dictionary” 6 th ed., The Cosmetic, Toiletry and Fragrance Association, Inc., Washington, 1995.
  • the active compound While lower concentrations of the active compound show an effect in a cell culture system, as can be seen from the examples, higher concentrations in personal care products are necessary to allow for an effective concentration on the human skin even if, for example part of the product may be removed by abrasion of clothes or may be diluted by sweat. Furthermore, the healthy skin acts as a barrier which limits the penetration of the active compounds.
  • the concentration of active compound needed for efficaciousness on skin is from about 50 to 100 times higher than that needed in in-vitro tests.
  • the usual perfume concentration in a topical cosmetic product is about 0.3 to 2% by weight. In general, the amount of actives applied is in the range of from 0.2 to 2% by weight, based on the end-product applied to the skin, the amounts applied usually being in the range of from 0.3 to 1% by weight.
  • the present invention refers in a further aspect to fragrance compositions comprising at least 30 weight % based on the total fragrance composition of at least two actives for reducing skin irritation as hereinabove described.
  • a fragrance composition comprising more than 40 weight % of active compounds should preferably contain at least 4 different actives
  • a fragrance composition comprising more than 50 weight % of active compounds should preferably contain at least 5 different actives
  • a fragrance compositions comprising more than 60 weight % of active compounds should preferably contain at least 6 different actives.
  • the present invention refers to fragrance compositions comprising at least 30 weight % of at least three, four or five actives for reducing skin irritation.
  • the fragrance composition according to the present invention comprises at least two, three or four actives of which are selected from a different group of compounds, namely group (a), (b), (c), (d), (e), and (f) as hereinabove described.
  • fragrance compositions comprising a compound of formula (a) and a compound of formula (b), and fragrance compositions comprising a compound of formula (c) and a compound of formula (d) or (d′).
  • fragrance compositions which are both hedonically attractive and which have irritation reducing properties may be prepared, for example, if the composition comprises at least four active compounds, each of which is selected from a different group of compounds.
  • topical skin care compositions such as cosmetic products and personal wash products, comprising about 0.2 to about 3 weight %, preferably about 0.5 to about 2.5 weight % of a fragrance composition, the fragrance composition containing at least 30 weight % of at least two actives selected from the group (a), (b), (c), (d), (e), and (f) as hereinabove described, with the proviso that the topical skin care composition comprises at least 0.2 weight % of actives based on the total amount of the skin composition.
  • topical skin care compositions wherein the fragrance composition containing a compound of formula (a) and a compound of formula (b), and topical skin care composition wherein the fragrance composition containing a compound of formula (c) and a compound of formula (d) or (d′).
  • the present invention is directed to a method of reducing the onset of skin irritation by applying to the skin an effective amount of a topical skin care composition comprising a fragrance composition, the fragrance composition containing at least 30 weight % based on the total fragrance composition of at least two actives as defined hereinabove, with the proviso that the topical skin care composition comprises at least 0.2 weight % of actives based on the total amount of the skin composition.
  • an “effective amount” is generally achieved if about 5-50 mg/cm 2 skin or about 0.05 to about 0.5 mm thick film of the topical skin product is applied to the skin.
  • the expression “at least 30 weight %” includes fragrance compositions comprising at least 35, 40 or even 45 or 50 weight % of at least two actives as defined hereinabove.
  • actives and “active compounds” as used within the meaning of the present invention refers to all compounds selected from the list of compounds of formula (a), (b), (c), (d), (d′), (e) and 2-heptylcyclopentanone, 2-ethoxynaphthalene, 2-methoxynaphthalene, 1-methoxy-4-(prop-1-enyl)benzene and 1-(cyclopropylmethyl)-4-methoxybenzene.
  • Topical skin care compositions of the present invention may be divided into two classes of products, that is, cosmetic products and topical washing products, and may include but is not limited to antiperspirants, deodorants, day and night creams, shaving products, hand creams, body lotions, hair shampoo and conditioners, lipsticks, after-sun products, hand lotions, foundation creams, moisturizing creams, skin food, skin tonics, skin lightening products and overnight facial masks.
  • the compositions may be in any form. These forms may include lotions, creams, sticks, roll-on formulations, mousses, aerosol sprays, pad-applied formulations, powders, tonics, and emulsions (oil-in-water, water-in-oil, or mixed emulsion systems).
  • NHEK Normal human epidermal keratinocytes
  • keratinocyte growth medium supplemented with 10% heat inactivated fetal calf serum at a humidity of 98% in a 5% carbon dioxide atmosphere.
  • a confluent culture was trypsinated and adjusted to a density of 5 ⁇ 10 4 cells/ml.
  • the cells were then seeded in the same medium but with only 1% fetal calf serum in 24 well plates and cultivated for a period of 48 h.
  • a model irritating agent was then applied to the cells by adding calcimycin to a final level of 2.5 ⁇ M.
  • the individual compounds as listed below, dissolved in DMSO were added simultaneously. The final concentration of the compounds was 50 ⁇ M or 10 ⁇ M, the final DMSO concentration was adjusted to 1% (v/v). Parallel treatments received no calcimycin (non-irritated control) or calcimycin without compounds according to the present invention (irritated control). The DMSO concentration was adjusted to 1% in all these control treatments. After 24 h incubation, the supernatant of the cells was harvested, diluted 1:1 and added to an enzyme linked immunoassay kit for the specific detection of prostaglandin E 2 as a marker of cellular irritation (Product # 404110, Neogen corporation, Lexington Ky. 40505, USA). The prostaglandin levels in treated cell cultures were compared to the irritated and non-irritated control cultures in order to determine the relative inhibition of PGE 2 formation. Results for the individual compounds are listed below.
  • the fragrance composition No. 7 comprises 37.2 weight % of actives.
  • Keratinocytes were grown in 24 well plates and irritated with calcimycin as described in example 1. Fragrance compositions of example 2 were dissolved in DMSO and added to the cultures simultaneously. Inhibition of PGE 2 formation was measured as described in example 1. The results are listed in Table 1.
  • a hydrogel was prepared as follows:
  • An antiperspirant was formulated according the following formulation:
  • antiperspirants formulated with conventional perfumes led to significantly enhanced PGE 2 formation indicating an irritating nature of these products to the human skin, whereas upon treatment of EpiDerm with antiperspirants containing the inventive fragrance composition, no significantly enhanced PGE 2 levels were detected. All epidermal cultures retained 100% of the cellular viability showing that all the products are not cytotoxic.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Emergency Medicine (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Fats And Perfumes (AREA)
US12/066,518 2005-09-12 2006-09-08 Organic compounds Abandoned US20100063011A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GBGB0518558.2A GB0518558D0 (en) 2005-09-12 2005-09-12 Improvements in or related to organic compounds
GB0518558.2 2005-09-12
PCT/CH2006/000481 WO2007030961A2 (fr) 2005-09-12 2006-09-08 Composes organiques ameliores

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/CH2006/000481 A-371-Of-International WO2007030961A2 (fr) 2005-09-12 2006-09-08 Composes organiques ameliores

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US13/006,791 Division US9440097B2 (en) 2005-09-12 2011-01-14 Organic compounds

Publications (1)

Publication Number Publication Date
US20100063011A1 true US20100063011A1 (en) 2010-03-11

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Family Applications (3)

Application Number Title Priority Date Filing Date
US12/066,518 Abandoned US20100063011A1 (en) 2005-09-12 2006-09-08 Organic compounds
US13/006,791 Active 2030-07-18 US9440097B2 (en) 2005-09-12 2011-01-14 Organic compounds
US15/235,587 Active 2026-09-28 US10512599B2 (en) 2005-09-12 2016-08-12 Organic compounds

Family Applications After (2)

Application Number Title Priority Date Filing Date
US13/006,791 Active 2030-07-18 US9440097B2 (en) 2005-09-12 2011-01-14 Organic compounds
US15/235,587 Active 2026-09-28 US10512599B2 (en) 2005-09-12 2016-08-12 Organic compounds

Country Status (8)

Country Link
US (3) US20100063011A1 (fr)
EP (1) EP1968531B1 (fr)
JP (1) JP2009509929A (fr)
CN (1) CN101262843B (fr)
BR (1) BRPI0615927B1 (fr)
GB (1) GB0518558D0 (fr)
MX (1) MX2008002811A (fr)
WO (1) WO2007030961A2 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110002880A1 (en) * 2007-12-05 2011-01-06 3-D Matrix, Ltd. Material For Wound Healing and Skin Reconstruction
US10238592B2 (en) * 2014-04-28 2019-03-26 Givaudan S.A. Organic compounds

Families Citing this family (6)

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Publication number Priority date Publication date Assignee Title
JP5248114B2 (ja) * 2004-12-08 2013-07-31 ジボダン エス エー 有機化合物
JP4841208B2 (ja) * 2005-09-12 2011-12-21 高砂香料工業株式会社 フレーバー及びフレグランス組成物
WO2008055372A1 (fr) * 2006-11-07 2008-05-15 Givaudan Sa Compositions de neutralisation des mauvaises odeurs
GB201021050D0 (en) * 2010-12-13 2011-01-26 Givaudan Sa Moc compositions
EP2921161B2 (fr) * 2012-11-15 2021-09-01 Shiseido Company Ltd. Inhibiteur de la production de mélanine
KR101796866B1 (ko) * 2016-06-28 2017-11-13 연세대학교 산학협력단 시멘, 베헨산, 2-메톡시나프탈렌, 티몰 및 이들의 염으로 이루어진 군에서 선택된 어느 하나 이상을 유효성분으로 함유하는 피부보습 개선, 피부각질 제거, 피부탄력 증진, 홍반 억제, 피부주름 개선 또는 피부광노화 개선 효과를 갖는 조성물

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4657700A (en) * 1983-10-07 1987-04-14 Givaudan Corporation Fragrance compositions containing benzyl ethers
US5389608A (en) * 1994-05-12 1995-02-14 International Flavors & Fragrances Inc. 1-phenyl-1-cyano-C5 -C7 alkanes, organoleptic uses thereof and process for preparing same
US6069125A (en) * 1995-11-01 2000-05-30 Givaudan Roure (International) Sa Nitrile
US20010005711A1 (en) * 1999-12-21 2001-06-28 Stefan Lambrecht Perfume compositions comprising 4,8-dimethyl-3,7-nonadien-2-one

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110002880A1 (en) * 2007-12-05 2011-01-06 3-D Matrix, Ltd. Material For Wound Healing and Skin Reconstruction
US10238592B2 (en) * 2014-04-28 2019-03-26 Givaudan S.A. Organic compounds

Also Published As

Publication number Publication date
US9440097B2 (en) 2016-09-13
WO2007030961A3 (fr) 2007-05-03
CN101262843A (zh) 2008-09-10
US20160346181A1 (en) 2016-12-01
US20120184513A1 (en) 2012-07-19
JP2009509929A (ja) 2009-03-12
US10512599B2 (en) 2019-12-24
CN101262843B (zh) 2013-01-30
WO2007030961A2 (fr) 2007-03-22
EP1968531B1 (fr) 2014-12-31
BRPI0615927A2 (pt) 2011-05-31
GB0518558D0 (en) 2005-10-19
BRPI0615927B1 (pt) 2016-09-06
MX2008002811A (es) 2008-04-07
EP1968531A2 (fr) 2008-09-17

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