22567-17-5

Basic information

• Product Name: (+)-GAMMA-GURJUNENE
• Synonyms: (+)-GAMMA-GURJUNENE;(3R,6R,7R,10R)-6,10-DIMETHYL-3-ISOPROPENYL-BICYCLO[5.3.0]DEC-1-ENE;1beta,4betaH,10betaH-Guaia-5,11-diene;7-Isopropenyl-1,4-dimethyl-1,2,3,3a,4,5,6,7-octahydroazulene;Azulene, 1,2,3,3a,4,5,6,7-octahydro-1,4-dimethyl-7-(1-methylethenyl)-, [1R-(1alpha,3abeta,4alpha,7beta)]-;[1R-(1alpha,3abeta,4alpha,7beta)]-1,2,3,3a,4,5,6,7-octahydro-7-isopropenyl-1,4-dimethylazulene;(+)-GAMMA-GURJUNENE 97+%;(1R)-1,2,3,3aβ,4,5,6,7-Octahydro-1α,4α-dimethyl-7β-(1-methylethenyl)azulene
• CAS NO: 22567-17-5
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.35
• EINECS: 245-084-1
• Mol File: 22567-17-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 264-266 °C(lit.)
• Flash Point: 110 °C
• Appearance: /
• Density: 0.918 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.008mmHg at 25°C
• Refractive Index: n20/D 1.502
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (+)-GAMMA-GURJUNENE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-GAMMA-GURJUNENE(22567-17-5)
• EPA Substance Registry System: (+)-GAMMA-GURJUNENE(22567-17-5)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• F: 8-10-23
• Hazardous Substances Data: 22567-17-5(Hazardous Substances Data)

Usage

General Description

(+)-Gamma-Gurjunene is a natural organic compound found in a variety of aromatic plants, particularly in the essential oil of the Gurjun balsam tree. It is a sesquiterpene that contributes to the characteristic scent of these plants and has been utilized in traditional medicine for its potential therapeutic properties. It is also used in the fragrance industry for its woody and spicy aroma. Studies have shown that (+)-Gamma-Gurjunene possesses anti-inflammatory and antimicrobial properties, making it a promising candidate for the development of new pharmaceutical and cosmetic products. Additionally, it has potential industrial applications due to its chemical structure and reactivity.

InChI:InChI=1/C15H24/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h9,11-14H,1,5-8H2,2-4H3/t11-,12-,13-,14-/m1/s1

Synthetic route

(1aR,4R,7R,7bS)-1,1,4,7-tetramethyl-1a,2,3,4,5,6,7,7b-octahydro-1H-cyclopropa[e]azulene (29484-27-3, 95910-36-4, 110769-61-4) → [1R-(1α,3aβ,4α,7β)]-1,2,3,3a,4,5,6,7-octahydro-1,4-dimethyl-7-(1-methylethenyl)-azulene (22567-17-5)

Conditions	Yield
at 450℃;	80%

(+)-aromadendrene (489-39-4, 552-01-2, 14682-34-9, 14682-39-4, 14682-40-7, 14682-42-9, 25246-27-9, 55721-09-0, 72747-25-2, 74036-37-6, 97950-10-2, 109119-91-7, 125133-80-4, 146389-60-8) → [1R-(1α,3aβ,4α,7β)]-1,2,3,3a,4,5,6,7-octahydro-1,4-dimethyl-7-(1-methylethenyl)-azulene (22567-17-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: K/Al2O3 / 100 °C 2: 80 percent / 450 °C View Scheme
Multi-step reaction with 2 steps 1: 100 percent / 10percent K/Al2O3 / hexane / Ambient temperature 2: 80 percent / 450 °C View Scheme

[1R-(1α,3aβ,4α,7β)]-1,2,3,3a,4,5,6,7-octahydro-1,4-dimethyl-7-(1-methylethenyl)-azulene (22567-17-5) → (6R,10R)-3-Isopropyl-6,10-dimethyltricyclo[5.3.0]deca-2,7(1)-diene (111900-51-7)

Conditions	Yield
With fluorosulfonylchloride In dichloromethane at -115℃; Isomerization;	33%

[1R-(1α,3aβ,4α,7β)]-1,2,3,3a,4,5,6,7-octahydro-1,4-dimethyl-7-(1-methylethenyl)-azulene (22567-17-5) → (3R,6R,7R,10R)-1β,2β-epoxy-6,10-dimethyl-3-isopropenylbicyclo[5.3.0]decane + (2)-γ-gurjunenepoxide + (3R,6R,7R,10R)-1β,2β-epoxy-6,10-dimethyl-3-(11α,12-epoxy)isopropylbicyclo[5.3.0]decane + (3R,6R,7R,10R)-1β,2β-epoxy-6,10-dimethyl-3-(11β,12-epoxy)isopropylbicyclo[5.3.0]decane

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 25℃; for 12h; Product distribution; var. temp. and time;	A 36 mg B 24 mg C 56 mg D 13 mg
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 25℃; for 12h;	A 36 mg B 24 mg C 56 mg D 13 mg
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 25℃; for 4h;	A 36 mg B 24 mg C 56 mg D 13 mg

[1R-(1α,3aβ,4α,7β)]-1,2,3,3a,4,5,6,7-octahydro-1,4-dimethyl-7-(1-methylethenyl)-azulene (22567-17-5) → 2-((3R,5R,8R,8aR)-3,8-Dimethyl-1,2,3,5,6,7,8,8a-octahydro-azulen-5-yl)-propane-1,2-diol + 2-((3R,5R,8S,8aS)-8-Hydroxy-3,8-dimethyl-1,2,3,5,6,7,8,8a-octahydro-azulen-5-yl)-propane-1,2-diol

Conditions	Yield
With Glomerella cingulata In water for 240h; culture medium;	A 202 mg B 68 mg

[1R-(1α,3aβ,4α,7β)]-1,2,3,3a,4,5,6,7-octahydro-1,4-dimethyl-7-(1-methylethenyl)-azulene (22567-17-5) → (1aR,4R,7R,7bS)-1,1,4,7-tetramethyl-1a,2,3,4,5,6,7,7b-octahydro-1H-cyclopropa[e]azulene (29484-27-3, 95910-36-4, 110769-61-4) + (6R,7R)-3-Isopropyl-6,10-dimethyltricyclo[5.3.0]deca-2,7(1)-diene (113561-07-2) + (8R,8aR)-5-Isopropyl-3,8-dimethyl-1,2,6,7,8,8a-hexahydro-azulene + (1S,4R)-7-Isopropyl-1,4-dimethyl-1,2,3,4,5,6-hexahydro-azulene

Conditions	Yield
With Sulfate; titanium(IV) oxide In dichloromethane at 20℃; for 0.216667h; Rearrangement;	A n/a B 0.0514 g C 0.0048 g D n/a

[1R-(1α,3aβ,4α,7β)]-1,2,3,3a,4,5,6,7-octahydro-1,4-dimethyl-7-(1-methylethenyl)-azulene (22567-17-5) → (1R,3aR,7R,8aR)-7-Isopropyl-1,4-dimethyl-decahydro-azulene

Conditions	Yield
With hydrogen; nickel on carbon In ethanol; benzene at 25℃;

[1R-(1α,3aβ,4α,7β)]-1,2,3,3a,4,5,6,7-octahydro-1,4-dimethyl-7-(1-methylethenyl)-azulene (22567-17-5) → (1S,4S,7R,10R)-5,11(13)-guaiadiene-12-ol

Conditions	Yield
With chicory; enzymes from roots of Cichorium intybus L; NADPH In ethanol for 1h; pH=7.5; Product distribution; Further Variations:; Reagents; Solvents;

Upstream product

• 489-39-4 (+)-aromadendrene 
• 29484-27-3 (1aR,4R,7R,7bS)-1,1,4,7-tetramethyl-1a,2,3,4,5,6,7,7b-octahydro-1H-cyclopropa[e]azulene