CN106167508A - A kind of glucoside compounds with violet fragrance and preparation method thereof - Google Patents
A kind of glucoside compounds with violet fragrance and preparation method thereof Download PDFInfo
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- CN106167508A CN106167508A CN201610548672.5A CN201610548672A CN106167508A CN 106167508 A CN106167508 A CN 106167508A CN 201610548672 A CN201610548672 A CN 201610548672A CN 106167508 A CN106167508 A CN 106167508A
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- glucoside
- compound
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- fragrance
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/18—Acyclic radicals, substituted by carbocyclic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
- C07H15/10—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical containing unsaturated carbon-to-carbon bonds
Abstract
The invention provides a kind of glucoside compounds with violet fragrance, its general structure is:Or
Description
Technical field
The invention belongs to chemical field, relate to a kind of glucoside compounds, one has violet incense specifically
Glucoside compounds of taste and preparation method thereof.
Background technology
Violet incense has refreshment, allaying tiredness, promotes the effects such as respiratory system is unobstructed.But carry from violet
The pure the most loaded down with trivial details yield of these perfume compounds is low, and the mixture obtained often is mixed with a large amount of impurity thus reduces fragrance
Quality.The compound then with violet fragrance is developed, and the most representational is some alcohol compound.
But, these alcohol compounds have stronger volatility and case of thermal instability, As time goes on, fragrant
Taste and medicinal efficacy can die down.Additionally, this type of alcohol compound poorly water-soluble, need bigger organic molten of cooperation toxicity
Agent uses after dissolving.Therefore raising heat stability and water solublity are the keys that this type of alcohol compound maximum plays effect and effect.
And alcohol molecule and glucose combination are prepared as glucoside compounds is a kind of very effective method.Known
There are menthol glucoside (J Agric Food Chem 2,001 49 5888), phenethanol glucoside (Biosci
Biotech Biochem 1,994 58 (8) 1532) etc. report.These glucoside compounds in placement process by pyrolysis,
The process slow release such as photodissociation, hydrolysis goes out fragrance alcohol molecule, thus is greatly improved the stability of alcohol molecule so that these alcohol molecules
Performance effect that energy is lasting.
Summary of the invention
For above-mentioned technical problem of the prior art, the invention provides a kind of glucoside with violet fragrance
Compound and preparation method thereof, described this glucoside compounds with violet fragrance and preparation method thereof to solve
Alcohol compound case of thermal instability of the prior art and the technical problem of poorly water-soluble.
The invention provides a kind of glucoside compounds with violet fragrance, its general structure is:
OrWherein, P is H or acetyl group.
Present invention also offers above-mentioned a kind of glucoside compounds with violet fragrance, comprise the steps:
(1) tetra-acetylated replacement glucose bromo-derivative (IV) and alcohol (III) react and obtain tetra-acetylated replacement glucoside (II),
Wherein ROH is
Or
(2) tetra-acetylated replacement glucoside (II) deacetylation obtains glucoside (I),
Further, the reaction preparing compound (II) is carried out under carbonate effect, and carbonate used is selected from
Any one in Disilver carbonate, chromium carbonate or potassium carbonate.
Further, the reaction preparing compound (II) is carried out under organic solvent effect, organic solvent used
Any one in N,N-dimethylformamide, dichloromethane, chloroform, oxolane, acetonitrile, toluene or acetone
Kind.
Further, the reaction preparing compound (I) is carried out under Feldalat NM and methanol effect.
Concrete, the structure of the glucoside compounds with violet fragrance is the tetra-acetylated glucose of violet leaf alcohol
Glycosides (II a) or violet leaf alcohol glucoside (I a):
Concrete, the structure of the glucoside compounds with violet fragrance is 4-methyl-3-certain herbaceous plants with big flowers alkene-5-alcohol four acetyl
Base glucoside (II b) or 4-methyl-3-certain herbaceous plants with big flowers alkene-5-alcohol glucoside (I b):
Concrete, the structure of the glucoside compounds with violet fragrance is the tetra-acetylated glucose of α-ionol
Glycosides (II c) or α-ionol glucoside (I c):
Concrete, the structure of the glucoside compounds with violet fragrance is the tetra-acetylated glucose of β-ionol
Glycosides (II d) or β-ionol glucoside (I d):
Above-mentioned reaction with alcohol (III) from tetra-acetylated replacement glucose bromo-derivative (IV) obtains tetra-acetylated replacement glucose
The operating process of the reaction of glycosides (II) approximately as: in reaction bulb, add compound (IV), alcohol (III), carbonate and molten
Agent, reacts 1-72h at appropriate temperatures.After removal of solvent under reduced pressure, column chromatography for separation, obtain compound (II).
The operating process of the above-mentioned reaction obtaining glucoside (I) from tetra-acetylated replacement glucoside (II) deacetylation
Approximately as: in reaction bulb, add compound (II), Feldalat NM and methanol, react 1-24h at appropriate temperatures.Neutralize
After, after removal of solvent under reduced pressure, column chromatography for separation, obtain compound (I).
The present invention utilize glucose be combined with alcohol be prepared for having violet fragrance glucoside compounds, it has
The feature such as stability height, water solublity height, pure fragrance.
The advantage of the method for the present invention is, by brief step, to be prepared for the chemical combination with violet fragrance easily
Thing.
Detailed description of the invention
Further illustrate technical scheme with specific embodiment below, but protection scope of the present invention is not limited to
This:
The synthesis of the tetra-acetylated glucoside of embodiment 1 violet leaf alcohol (II a)
2g compound (IV), 0.34g violet leaf alcohol (III a), 0.73g Disilver carbonate and 10mL bis-is added in reaction bulb
Chloromethanes, reacts 24 hours under room temperature.Removal of solvent under reduced pressure, by column chromatography for separation, eluant (petrol ether/ethyl acetate=
5/1) 0.85g white solid is swept away, for compound (II a):
1H NMR(400MHz,CDCl3) δ: 0.96 (t, J=8Hz, 3H), 2.00-2.06 (m, 3H), 2.01-2.09 (4s,
12H), 2.05-2.14 (m, 3H), 3.65-3.70 (m, 1H), 4.05 (dd, J=7.2,12.4Hz, 1H), 4.14 (dd, J=
2.4,12.4Hz, 1H), 4.24-4.30 (m, 2H), 4.55 (d, J=8.4Hz, 1H), 5.00 (dd, J=8.0,9.6Hz, 1H),
5.09 (t, J=9.2Hz, 1H), 5.21 (t, J=9.2Hz, 1H), 5.28-5.29 (m, 1H), 5.37-5.43 (m, 1H), 5.46-
5.53(m,1H),5.66-5.74(m,1H)
The synthesis of embodiment 2 violet leaf alcohol glucoside (I a)
0.5g compound (II a), 0.23g Feldalat NM, 5mL methanol, room temperature reaction 24 hours is added in reaction bulb.Add
Hydrogen chloride methanol solution neutralizes, removal of solvent under reduced pressure, and by column chromatography for separation, eluant (methylene chloride/methanol=10/1) rushes
Lower 0.29g white solid, for compound (I a):
1H NMR (400MHz, MeOD) δ: 0.95 (t, J=7.2Hz, 3H), 2.00-2.08 (m, 3H), 2.09-2.15 (m,
3H), 3.15-3.25 (m, 1H), 3.26-3.35 (m, 3H), 3.65 (dd, J=6.0,12.0Hz, 1H), 3.85 (dd, J=2.0,
9.0Hz, 1H), 4.09 (dd, J=2.4,9.0Hz, 1H), 4.25-4.34 (m, 2H), 4.85 (br, 4H), 5.29-5.41 (m,
2H),5.57-5.65(m,1H),5.73-5.79(m,1H)
The synthesis of the embodiment 3 4-methyl-3-certain herbaceous plants with big flowers alkene tetra-acetylated glucoside of-5-alcohol (II b)
2g compound (IV), 0.41g 4-methyl-3-certain herbaceous plants with big flowers alkene-5-alcohol (III b), 0.73g Disilver carbonate is added in reaction bulb
And 10mL dichloromethane, react 24 hours under room temperature.Removal of solvent under reduced pressure, by column chromatography for separation, eluant (petroleum ether/
Ethyl acetate=5/1) sweep away 0.47g half half aqueous material admittedly, for compound (II b):
1H NMR(400MHz,CDCl3)δ:0.85-0.89(m,3H),0.94-1.01(m,3H),1.11-1.18(m,1H),
1.19-1.22(m,6H),1.40-1.46(m,2H),1.58-1.65(m,1H),2.00-2.11(5s,15H),3.55-3.95
(m, 2H), 3.98-4.30 (m, 2H), 4.44 (dd, J=8.4,16.8Hz, 1H), 4.97-5.10 (m, 2H), 5.15-5.19 (m,
1H),5.53-5.36(m,1H)
The synthesis of embodiment 4 4-methyl-3-certain herbaceous plants with big flowers alkene-5-alcohol glucoside (I b)
0.4g compound (II b), 0.17g Feldalat NM, 4mL methanol, room temperature reaction 24 hours is added in reaction bulb.Add
Hydrogen chloride methanol solution neutralizes, removal of solvent under reduced pressure, and by column chromatography for separation, eluant (methylene chloride/methanol=10/1) rushes
Lower 0.24g colorless oil, for compound (I b):
1H NMR(400MHz,MeOD)δ:0.76-0.82(m,3H),0.85-0.99(m,3H),1.20-1.30(m,6H),
1.48-1.75(m,5H),2.00-2.09(m,2H),3.10-3.33(m,3H),3.61-4.23(m,5H),4.85(br,4H),
5.32-5.45(m,1H)
The synthesis of the tetra-acetylated glucoside of embodiment 5 α-ionol (II c)
2g compound (IV), 0.47g a-ionol (III c), 0.73g Disilver carbonate and 10mL is added in reaction bulb
Dichloromethane, reacts 24 hours under room temperature.Removal of solvent under reduced pressure, by column chromatography for separation, eluant (petrol ether/ethyl acetate
=5/1) 0.57g faint yellow solid is swept away, for compound (II c):
The synthesis of embodiment 6 α-ionol glucoside (I c)
0.5g compound (II c), 0.2g Feldalat NM, 5mL methanol, room temperature reaction 24 hours is added in reaction bulb.Add
Hydrogen chloride methanol solution neutralizes, removal of solvent under reduced pressure, and by column chromatography for separation, eluant (methylene chloride/methanol=10/1) rushes
Lower 0.32g faint yellow solid, for compound (I c):
The synthesis of the tetra-acetylated glucoside of embodiment 7 β-ionol (II d)
2g compound (IV), 0.47g b-ionol (III d), 0.73g Disilver carbonate and 10mL is added in reaction bulb
Dichloromethane, reacts 24 hours under room temperature.Removal of solvent under reduced pressure, by column chromatography for separation, eluant (petrol ether/ethyl acetate
=5/1) 0.59g faint yellow solid is swept away, for compound (II d):
The synthesis of embodiment 8 β-ionol glucoside (I d)
0.5g compound (II d), 0.2g Feldalat NM, 5mL methanol, room temperature reaction 24 hours is added in reaction bulb.Add
Hydrogen chloride methanol solution neutralizes, removal of solvent under reduced pressure, and by column chromatography for separation, eluant (methylene chloride/methanol=10/1) rushes
Lower 0.34g faint yellow solid, for compound (I d).
Claims (5)
1. a glucoside compounds with violet fragrance, it is characterised in that its general structure is:
Wherein, P is H or acetyl group.
2. a kind of glucoside compounds with violet fragrance described in claim 1, it is characterised in that include walking as follows
Rapid:
(1) tetra-acetylated replacement glucose bromo-derivative (IV) and alcohol (III) react and obtain tetra-acetylated replacement glucoside (II),
Wherein ROH is
(2) tetra-acetylated replacement glucoside (II) deacetylation obtains glucoside (I),
A kind of glucoside compounds with violet fragrance the most according to claim 2, it is characterised in that: preparationization
The reaction of compound (II) is carried out under carbonate effect, and carbonate used is selected from Disilver carbonate, chromium carbonate or potassium carbonate
In any one.
A kind of glucoside compounds with violet fragrance the most according to claim 2, it is characterised in that: preparationization
The reaction of compound (II) is carried out under organic solvent effect, organic solvent used selected from DMF, two
Any one in chloromethanes, chloroform, oxolane, acetonitrile, toluene or acetone.
A kind of glucoside compounds with violet fragrance the most according to claim 2, it is characterised in that: preparationization
The reaction of compound (I) is carried out under Feldalat NM and methanol effect.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201610548672.5A CN106167508A (en) | 2016-07-13 | 2016-07-13 | A kind of glucoside compounds with violet fragrance and preparation method thereof |
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| CN201610548672.5A CN106167508A (en) | 2016-07-13 | 2016-07-13 | A kind of glucoside compounds with violet fragrance and preparation method thereof |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106986903A (en) * | 2017-03-07 | 2017-07-28 | 上海应用技术大学 | A kind of cigarette fragrance materials and its preparation method and application |
| CN109970826A (en) * | 2019-04-22 | 2019-07-05 | 上海应用技术大学 | Glucoside compounds and preparation method thereof containing tertiary base carbon atom |
| CN111763569A (en) * | 2020-07-10 | 2020-10-13 | 湖北中烟工业有限责任公司 | Fragrance-variable essence and flavor and synthesis method thereof |
| WO2023072085A1 (en) * | 2021-10-25 | 2023-05-04 | 陈令仪 | Isopropyl-d-glucopyranoside derivative, and preparation method therefor and use thereof |
Citations (1)
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| CN102617659A (en) * | 2012-03-09 | 2012-08-01 | 中国烟草总公司郑州烟草研究院 | Synthesis method for alpha-ionol glucoside, and application of alpha-ionol glucoside to flavoring of cigarettes |
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2016
- 2016-07-13 CN CN201610548672.5A patent/CN106167508A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102617659A (en) * | 2012-03-09 | 2012-08-01 | 中国烟草总公司郑州烟草研究院 | Synthesis method for alpha-ionol glucoside, and application of alpha-ionol glucoside to flavoring of cigarettes |
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| D. MCGINTY，ET AL.: ""Fragrance material review on (2E,6Z)-nona-2,6-dien-1-ol"", 《FOOD AND CHEMICAL TOXICOLOGY》 * |
| SHITONG ZENG，ET AL.: ""Synthesis of a-ionyl-b-D-glucoside and its property of flavor"", 《J THERM ANAL CALORIM》 * |
| 孟广宇，等: ""β-紫罗兰醇-β-D-葡糖苷的合成及热解性质"", 《食品科学》 * |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106986903A (en) * | 2017-03-07 | 2017-07-28 | 上海应用技术大学 | A kind of cigarette fragrance materials and its preparation method and application |
| CN106986903B (en) * | 2017-03-07 | 2019-07-19 | 上海应用技术大学 | A kind of cigarette fragrance materials and its preparation method and application |
| CN109970826A (en) * | 2019-04-22 | 2019-07-05 | 上海应用技术大学 | Glucoside compounds and preparation method thereof containing tertiary base carbon atom |
| CN111763569A (en) * | 2020-07-10 | 2020-10-13 | 湖北中烟工业有限责任公司 | Fragrance-variable essence and flavor and synthesis method thereof |
| CN111763569B (en) * | 2020-07-10 | 2023-08-25 | 湖北中烟工业有限责任公司 | Fragrance-changeable essence and spice and synthesis method thereof |
| WO2023072085A1 (en) * | 2021-10-25 | 2023-05-04 | 陈令仪 | Isopropyl-d-glucopyranoside derivative, and preparation method therefor and use thereof |
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