489-41-8

Basic information

• Product Name: (-)-GLOBULOL
• Synonyms: (-)-GLOBULOL;GLOBULOL, (-)-;[1aR-(1aalpha,4alpha,4aalpha,7alpha,7abeta,7balpha)]-decahydro-1,1,4,7-tetramethyl-1H-cycloprop[e]azulen-4-ol;(-)-GLOBULOL PURISS 98.5%;(1aR,4aβ,7aα,7bβ)-Decahydro-1,1,4,7β-tetramethyl-1H-cycloprop[e]azulen-4β-ol;(1R,3aα,8aβ)-1α,4-Dimethyl-7β,8β-isopropylidenedecahydroazulene-4α-ol;10-Aromadendranol;1aβ,2,3,4,4aβ,5,6,7,7aα,7bβ-Decahydro-1,1,4,7β-tetramethyl-1H-cyclopropa[e]azulene-4β-ol
• CAS NO: 489-41-8
• Molecular Formula: C15H26O
• Molecular Weight: 222.37
• EINECS: 207-696-7
• Mol File: 489-41-8.mol
• Article Data: 1

Chemical Properties

• Melting Point: 87-88 °C
• Boiling Point: 283°C
• Flash Point: 123.1°C
• Appearance: /
• Density: 0.962g/cm³
• Vapor Pressure: 0.000177mmHg at 25°C
• Refractive Index: 1.492
• PKA: 15.21±0.60(Predicted)
• BRN: 3195922
• CAS DataBase Reference: (-)-GLOBULOL(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-GLOBULOL(489-41-8)
• EPA Substance Registry System: (-)-GLOBULOL(489-41-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 489-41-8(Hazardous Substances Data)

Usage

Description

(-)-Globulol, a sesquiterpene, is isolated from Eucalyptus globulus Labill (Myrtaceae) fruits and leaves of Schinus areira. It is characterized by its sweet, fruity, and green flavor, making it a popular addition to various food products such as peppermint, orange mint, spearmint, and sweet bay. In addition to its sensory attributes, (-)-Globulol has been recognized for its antioxidant and antifungal properties.

Uses

Used in Food Industry:
(-)-Globulol is used as a flavoring agent for its sweet, fruity, and green taste, enhancing the flavor profiles of various food products such as peppermint, orange mint, spearmint, and sweet bay.
Used in Pharmaceutical Industry:
(-)-Globulol is used as an antioxidant agent for its ability to combat oxidative stress, which can contribute to the prevention and treatment of various diseases and conditions.
Used in Agricultural Industry:
(-)-Globulol is used as an antifungal agent to protect crops from fungal infections, thereby improving crop yield and quality.

InChI:InChI=1/C15H26O/c1-9-5-6-10-12(9)13-11(14(13,2)3)7-8-15(10,4)16/h9-13,16H,5-8H2,1-4H3

Synthetic route

Toluene-4-sulfonic acid (1aR,4R,4aR,7R,7aS,7bS)-4-hydroxy-1,1,7-trimethyl-decahydro-cyclopropa[e]azulen-4-ylmethyl ester (186318-55-8) → (-)-globulol (489-41-8)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 3h; Heating;	160 mg

(+)-aromadendrene (489-39-4) → (-)-globulol (489-41-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 900 mg / K3, K2CO3, OsO4 / 2-methyl-propan-2-ol; H2O / 24 h / Ambient temperature 2: pyridine / Ambient temperature 3: 160 mg / LiAlH4 / tetrahydrofuran / 3 h / Heating View Scheme

(1S,2S,4R,7R,8R,11R)-3,3,11-trimethyl-7-hydroxymethyl-tricyclo<6.3.0.02,4>undecan-7-ol (145988-09-6) → (-)-globulol (489-41-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / Ambient temperature 2: 160 mg / LiAlH4 / tetrahydrofuran / 3 h / Heating View Scheme

(+)-aromadendrene (489-39-4) → (-)-globulol (489-41-8) + 1,1,4,7-tetramethyldecahydro-1H-cyclopropa[e]azulen-4-ol (88728-58-9)

Conditions	Yield
With iron(III)-acetylacetonate; 1,3-dibromo-5-fluoro-2-nitrobenzene; phenylsilane; sodium hydrogencarbonate In methanol at 0 - 20℃; for 12h; Reagent/catalyst; Schlenk technique; Inert atmosphere; Overall yield = 61 percent; diastereoselective reaction;	A n/a B n/a

(-)-globulol (489-41-8) → 6β,7α,14-trihydroxyaromadendrane (123735-83-1) + 7α,14-dihydroxyaromadendrane (123808-27-5) + 5α,7α-dihydroxyaromadendrane (186318-53-6)

Conditions	Yield
In ethanol for 144h; Mucor plumbeus;	A 1% B 58% C 1%

(-)-globulol (489-41-8) → (1S,2S,3S,4R,7R,8R,11R)-7-hydroxy-3,7,11-trimethyltricyclo<6.3.0.02,4>undecane-3-carboxylic acid (145941-01-1)

Conditions	Yield
In N,N-dimethyl-formamide for 96h; Mycobacterium smegmatis DSM 43061;	46%

(-)-globulol (489-41-8) → (+)-aromadendrene (489-39-4)

Conditions	Yield
With pyridine; trichlorophosphate

(-)-globulol (489-41-8) → 9-hydroxyglobulol (145940-99-4) + 6β,7α,14-trihydroxyaromadendrane (123735-83-1) + 9,14-exo-dihydroxyglobulol (145941-00-0) + 7α,14-dihydroxyaromadendrane (123808-27-5)

Conditions	Yield
In N,N-dimethyl-formamide for 28h; Bacillus megaterium DSM 32; Further byproducts given;	A 4 mg B 31 mg C 6 mg D 60 mg

(-)-globulol (489-41-8) → 6-hydroxyglobulol (145940-98-3) + 6β,7α,14-trihydroxyaromadendrane (123735-83-1) + 9,14-exo-dihydroxyglobulol (145941-00-0) + 7α,14-dihydroxyaromadendrane (123808-27-5)

Conditions	Yield
In N,N-dimethyl-formamide for 28h; Bacillus megaterium DSM 32; Further byproducts given;	A 8 mg B 31 mg C 6 mg D 60 mg

(-)-globulol (489-41-8) → 6-hydroxyglobulol (145940-98-3) + 6β,7α,14-trihydroxyaromadendrane (123735-83-1) + 14-endohydroxyglobulol (123808-26-4) + 7α,14-dihydroxyaromadendrane (123808-27-5)

Conditions	Yield
In N,N-dimethyl-formamide for 28h; Bacillus megaterium DSM 32; Further byproducts given;	A 8 mg B 31 mg C 2 mg D 60 mg

(-)-globulol (489-41-8) → 6β,7α,14-trihydroxyaromadendrane (123735-83-1) + 14-endohydroxyglobulol (123808-26-4) + 7α,14-dihydroxyaromadendrane (123808-27-5)

Conditions	Yield
In N,N-dimethyl-formamide for 48h; Displodia gossypina ATCC 10936; also with Bacillus megaterium DSM 32;	A 20 mg B 20 mg C 60 mg
In N,N-dimethyl-formamide for 48h; Diplodia gossypina ATCC 10936;	A 20 mg B 20 mg C 182 mg

(-)-globulol (489-41-8) → Aphidicolin (38966-21-1, 52645-92-8, 52645-96-2, 69926-98-3, 79254-70-9) + 7α,14-dihydroxyaromadendrane (123808-27-5)

Conditions	Yield
In dimethyl sulfoxide for 144h; biotransformation by Cephalosporium aphidicola;	A 93 mg B 780 mg

(-)-globulol (489-41-8) → 7α,14-dihydroxyaromadendrane (123808-27-5)

Conditions	Yield
for 432h; biotransformation by Glomerella cingulata;	921 mg

(-)-globulol (489-41-8) + Cephalosporium aphidicola → Aphidicolin (38966-21-1, 52645-92-8, 52645-96-2, 69926-98-3, 79254-70-9) + 7α,14-dihydroxyaromadendrane (123808-27-5)

Conditions	Yield
In dimethyl sulfoxide for 144h; biotransformation by Cephalosporium aphidicola;	A 93 mg B 780 mg

(-)-globulol (489-41-8) → Acetic acid (1aR,2S,4R,4aR,7R,7aS,7bS)-4-hydroxy-1,1,4,7-tetramethyl-decahydro-cyclopropa[e]azulen-2-yl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: 1 percent / ethanol / 144 h / Mucor plumbeus 2: pyridine View Scheme

(-)-globulol (489-41-8) → (1aR,4aR,7R,7aS,7bS)-1,1,7-Trimethyldecahydro-4H-cyclopropa[e]azulen-4-one (99147-41-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine; phosphoryl chloride 2: O3 View Scheme

(-)-globulol (489-41-8) → (1aR)-1,1,7c-trimethyl-(1ar,7at,7bc)-1a,2,3,5,6,7,7a,7b-octahydro-1H-cycloprop[e]azulene (109409-90-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: pyridine; phosphoryl chloride 2: O3 3: LiAlH4 / diethyl ether 4: POCl3 / pyridine View Scheme

(-)-globulol (489-41-8) → 1,1,7-trimethyl-decahydro-1H-cycloprop[e]azulen-4-ol (109435-87-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine; phosphoryl chloride 2: O3 3: LiAlH4 / diethyl ether View Scheme

(-)-globulol (489-41-8) → (1aR)-4ξ-hydroxymethyl-1,1,7c-trimethyl-(1ar,4ac,7at,7bc)-decahydro-cycloprop[e]azulen-4ξ-ol (95924-99-5, 97950-11-3, 145988-09-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine; phosphoryl chloride 2: (i) OsO4, Et2O, (ii) aq. KOH, benzene, EtOH, mannitol View Scheme

(-)-globulol (489-41-8) → apo-Aromadendren-diol

Conditions	Yield
Multi-step reaction with 5 steps 1: pyridine; phosphoryl chloride 2: O3 3: LiAlH4 / diethyl ether 4: POCl3 / pyridine 5: OsO4 / diethyl ether View Scheme

Upstream product

• 25246-27-9 alloaromadendrene 

Downstream Products

• 489-39-4 (+)-aromadendrene 
• 120830-19-5 (1aR)-4c-phenylcarbamoyloxy-1.1.4t.7c-tetramethyl-(1arH.4atH.7atH.7bcH)-decahydro-1H-cycloprop[e]-azulene 
• 21747-46-6 ledene 
• 38966-21-1 Aphidicolin 
• 123808-27-5 7β,14-dihydroxyaromadendrane 

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