22567-17-5

Usage

Uses

Used in Pharmaceutical Industry:
(+)-Gamma-Gurjunene is used as an active ingredient for its anti-inflammatory and antimicrobial properties, making it a promising candidate for the development of new pharmaceutical products. Its therapeutic potential can be harnessed to treat various conditions and diseases.
Used in Cosmetic Industry:
(+)-Gamma-Gurjunene is used as a key ingredient in cosmetic products for its anti-inflammatory and antimicrobial properties, contributing to the development of skincare and personal care products with natural and effective benefits.
Used in Fragrance Industry:
(+)-Gamma-Gurjunene is used as a fragrance component for its woody and spicy aroma, adding depth and complexity to perfumes, colognes, and other scented products.
Used in Traditional Medicine:
(+)-Gamma-Gurjunene is used in traditional medicine for its potential therapeutic properties, offering natural remedies and treatments for various ailments and conditions.
Used in Industrial Applications:
(+)-Gamma-Gurjunene is used in various industrial applications due to its chemical structure and reactivity, opening up possibilities for innovation and development in different sectors.

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

• 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 
• 489-39-4 (+)-aromadendrene