489-40-7

Basic information

• Product Name: (-)-ALPHA-GURJUNENE
• Synonyms: (-)-ALPHA-GURJUNENE;(2S,4R,7R,8R)-3,3,7,11-TETRAMETHYL-TRICYCLO[6.3.0.02.4]UNDEC-1(11)-ENE;(-)-α-gurjunene;1,1,4,7-Tetramethyl-1a,2,3,4,4a,5,6,7b-octahydro-1H-cyclopropa[e]azulene;1a,2,3,4,4a,5,6,7b-octahydro-1,1,4,7-tetramethyl-,[1aR-(1a.alpha.,4.alpha.,4a.beta.,7b.alpha.)]-1H-Cycloprop[e]azulene;1a,2,3,4,4a,5,6,7b-octahydro-1,1,4,7-tetramethyl-1h-cycloprop[e]azulen[1a;1H-Cycloprop[e]azulene, 1a,2,3,4,4a,5,6,7b-octahydro-1,1,4,7-tetramethyl-, (1aalpha,4alpha,4abeta,7balpha)-;1H-Cycloprop[e]azulene, 1a,2,3,4,4a,5,6,7b-octahydro-1,1,4,7-tetramethyl-, [1aR-(1aalpha,4alpha,4abeta,7balpha)]-
• CAS NO: 489-40-7
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.35
• EINECS: 207-695-1
• Mol File: 489-40-7.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 263.9°Cat760mmHg
• Flash Point: 110℃
• Appearance: /
• Density: 0.918 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.501
• Storage Temp.: 2-8°C
• BRN: 1939514
• CAS DataBase Reference: (-)-ALPHA-GURJUNENE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-ALPHA-GURJUNENE(489-40-7)
• EPA Substance Registry System: (-)-ALPHA-GURJUNENE(489-40-7)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 489-40-7(Hazardous Substances Data)

Usage

Description

(-)-ALPHA-GURJUNENE, also known as α-Gurjunene, is an essential oil extract derived from the plant Salvia tomentosa Miller. It is a natural sesquiterpene hydrocarbon with a distinct aroma and is known for its antimicrobial and antioxidant properties.

Uses

Used in Pharmaceutical Industry:
(-)-ALPHA-GURJUNENE is used as an antimicrobial agent for its ability to inhibit the growth of various microorganisms, making it a potential candidate for the development of new antibiotics and antifungal treatments.
Used in Cosmetics and Personal Care Industry:
(-)-ALPHA-GURJUNENE is used as an antioxidant agent for its ability to neutralize free radicals and protect the skin from oxidative stress, which can lead to premature aging and other skin conditions.
Used in Food and Beverage Industry:
(-)-ALPHA-GURJUNENE is used as a natural preservative for its antimicrobial properties, helping to extend the shelf life of various food and beverage products by preventing the growth of harmful bacteria and fungi.
Used in Aromatherapy:
(-)-ALPHA-GURJUNENE is used as a component in essential oil blends for its distinct aroma and potential therapeutic benefits, such as promoting relaxation and reducing stress.

Synthetic route

(-)-α-gurjunene (489-40-7) → (1S)-4c,8,8-trimethyl-3c-(3-oxo-butyl)-(1r,7c)-bicyclo[5.1.0]octan-2-one (41447-02-3)

Conditions	Yield
With potassium permanganate
(i) O3, AcOEt, (ii) aq. NaHSO3; Multistep reaction;

(-)-α-gurjunene (489-40-7) + diphenyldisulfane (882-33-7) → 7-isopropyl-1,4-dimethyl-azulene (489-84-9)

Conditions	Yield
at 250℃;

(-)-α-gurjunene (489-40-7) → (2R,3R,6R)-6-(1-Chloro-1-methyl-ethyl)-3-methyl-2-(3-oxo-butyl)-cycloheptanone

Conditions	Yield
(i) O3, AcOEt, (ii) aq. NaHSO3, (iii) aq. HCl, CCl4; Multistep reaction;

(-)-α-gurjunene (489-40-7) + acetic anhydride (108-24-7) → (3aR)-1,4t-Dimethyl-7c-<α-acetoxy-isopropyl>-(3arH)-3,3a,4,5,6,7-hexahydro-azulen (98032-77-0, 135248-36-1)

Conditions	Yield
With selenium(IV) oxide

(-)-α-gurjunene (489-40-7) → 5α-Cyclocoloran-4α-ol (1911-76-8, 87539-00-2)

Conditions	Yield
(i) B2H6, (ii) H2O2, aq. NaOH; Multistep reaction;

(-)-α-gurjunene (489-40-7) → 4α,5α-Cyclocoloran-3α-ol (489-44-1, 1786-21-6)

Conditions	Yield
(i) B2H6, (ii) H2O2, aq. NaOH; Multistep reaction;

(-)-α-gurjunene (489-40-7) → 1β,4ξ,5ξ,αH,10βH-Guaia-6ξ,12-diol

Conditions	Yield
(i) B2H6, (ii) H2O2, aq. NaOH; Multistep reaction;

hydrogenchloride (7647-01-0) + (-)-α-gurjunene (489-40-7) + acetic acid (64-19-7) → α-gurjunene hydrochloride

(-)-α-gurjunene (489-40-7) + acetic acid (64-19-7) + palladium → (-)-dihydro-α-gurjunene

Conditions	Yield
Hydrogenation;

(-)-α-gurjunene (489-40-7) + sulfuric acid (7664-93-9) + acetic acid (64-19-7) → (-)-iso-α-gurjunene

Conditions	Yield
at 60℃;

(-)-α-gurjunene (489-40-7) + bromine (7726-95-6) → 7-isopropyl-1,4-dimethyl-azulene (489-84-9)

hydrogenchloride (7647-01-0) + (-)-α-gurjunene (489-40-7) + acetic acid (64-19-7) → pseudo-α-gurjunene

Conditions	Yield
Kochen mit aethanol. KOH;

(-)-α-gurjunene (489-40-7) → cyclocolorenone (489-45-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: (i) B2H6, (ii) H2O2, aq. NaOH 2: CrO3, H2SO4 3: (i) tri-N-methyl-anilinium tribromide, (ii) Li2CO3, LiCl View Scheme

(-)-α-gurjunene (489-40-7) → 1α-Cyclocolor-4-en-3-on (489-45-2, 1911-75-7, 53584-68-2, 96895-11-3, 106190-33-4, 106190-34-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: (i) B2H6, (ii) H2O2, aq. NaOH 2: CrO3, H2SO4 3: (i) tri-N-methyl-anilinium tribromide, (ii) Li2CO3, LiCl 4: KOH View Scheme

(-)-α-gurjunene (489-40-7) → 2α-Brom-cyclocolor-4-en-3-on (1786-17-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: (i) B2H6, (ii) H2O2, aq. NaOH 2: CrO3, H2SO4 3: (i) tri-N-methyl-anilinium tribromide, (ii) Li2CO3, LiCl View Scheme

(-)-α-gurjunene (489-40-7) → 4α,5α-Cyclocoloran-3-on

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) B2H6, (ii) H2O2, aq. NaOH 2: CrO3, H2SO4 View Scheme

(-)-α-gurjunene (489-40-7) → (3aR)-1,4t-Dimethyl-7c-<α-hydroxy-isopropyl>-(3arH)-3,3a,4,5,6,7-hexahydro-azulen (135248-11-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: SeO2 2: LiAlH4 View Scheme

Downstream Products

• 489-45-2 Epicyclocolorenon 
• 489-45-2 cyclocolorenone 
• 489-84-9 7-isopropyl-1,4-dimethyl-azulene