alpha-Guaiene
Basic information
- CAS
3691-12-1- Standard SMILES
C=C(C)[C@@H]1CC[C@H](C)C2=C(C1)[C@@H](C)CC2- InChIKey
ADIDQIZBYUABQK-RWMBFGLXSA-N- Molecular formula
- C15H24
- Average molar mass
- 204.35 g/mol
- Monoisotopic mass
- 204.18780077
Overview
Alpha-guaiene is a carbobicyclic compound and sesquiterpene that is 1,2,3,4,5,6,7,8-octahydroazulene which is substituted by methyl groups at positions 1 and 4 and by a (prop-1-en-2-yl group at position 7 (the 1S,4S,7R enantiomer). It has a role as a volatile oil component and a plant metabolite. It is a sesquiterpene and a carbobicyclic compound.
Names & identifiers
- Preferred name
- alpha-Guaiene
- IUPAC
- (1S,4S,7R)-1,4-dimethyl-7-prop-1-en-2-yl-1,2,3,4,5,6,7,8-octahydroazulene
- English name
- α-guaiene,guaia-1(5),11-diene,[1S-(1a,4a,7a)]-1,2,3,4,5,6,7,8-octahydro-1,4-dimethyl-7-(1-methylethenyl)-azulene
- Molecular formula
- C15H24
- Molecular weight
- 204.35
Names & synonyms
alpha-Guaiene3691-12-1Guaia-1(5),11-diene(1S,4S,7R)-1,4-dimethyl-7-(prop-1-en-2-yl)-1,2,3,4,5,6,7,8-octahydroazuleneDTXSID5052046CHEBI:63443ABQ2CB7VACRefChem:27270DTXCID0030613(1S,4S,7R)-1,4-dimethyl-7-prop-1-en-2-yl-1,2,3,4,5,6,7,8-octahydroazuleneAzulene, 1,2,3,4,5,6,7,8-octahydro-1,4-dimethyl-7-(1-methylethenyl)-, [1S-(1.alpha.,4.alpha.,7.alpha.)]-alpha-quaiene
Show more names
α-Guaieneα-Guajenea-Guaienealfa-Guaieneα-Guaiene (>α-Guaiene (>85%)a-Guaiene (>85%)1,4-dimethyl-7-prop-1-en-2-yl-1,2,3,4,5,6,7,8-octahydroazulene(1S)-1,2,3,4,5,6,7,8-Octahydro-1,4β-dimethyl-7β-isopropenylazulene
orb2299261SCHEMBL196903477-Isopropenyl-1,4-dimethyl-1,2,3,4,5,6,7,8-octahydroazulene-, [1S-(1.alpha.,4.alpha.,7.alpha.)]-MFCD29767842TN7512HY-W587956C20161H53916
Properties
Computed structural properties
- XLogP
- 4.6
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 1
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 295
Experimental & physicochemical properties
FragrancesFragrance Ingredient (alpha-Guaiene) -> IFRA transparency List
Physicochemical properties
- Boiling point
- 78 · 78-79 °C(Press: 2.5 Torr)
- Density
- 0.8999 g/cm3 · 0.8999 g/cm3
- storage temp.
- Refrigerator, under inert atmosphere
- solubility
- Chloroform (Slightly), Dioxane (Sparingly, Sonicated), Methanol (Slightly)
- form
- Oil
- color
- Colourless to Pale Yellow
- Odor
- 100 % · at 100.00 %. sweet woody balsam peppery
- Odor Type
- woody
- Stability
- Light sensitive
- LogP
- 6.602 · 6.602 (est)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 2 CB7VAC · ABQ2CB7VAC
- EPA Substance Registry System
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H304 (100%): May be fatal if swallowed and enters airways [Danger Aspiration hazard]
P264, P264+P265, P280, P301+P316, P302+P352, P305+P351+P338, P321, P331, P332+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 164 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Azulene, 1,2,3,4,5,6,7,8-octahydro-1,4-dimethyl-7-(1-methylethenyl)-, [1S-(1.alpha.,4.alpha.,7.alpha.)]-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Hazard Classes and CategoriesAsp. Tox. 1 (100%)
Safety data
- tsca
- TSCA listed
- Signal word
- Danger
- Symbol(GHS)
- GHS07,GHS08
- Hazard statements
- H319-H304-H315
- Precautionary statements
- P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P
Chemistry & industry
Uses & manufacturing
Household ProductsInformation on 3 consumer products that contain alpha-Guaiene in the following categories is provided:
Use ClassificationFragrance Ingredients
General Manufacturing InformationAzulene, 1,2,3,4,5,6,7,8-octahydro-1,4-dimethyl-7-(1-methylethenyl)-, (1S,4S,7R)-: ACTIVE
Applications
Usesα-Guaiene is a sesquiterpene and an essential oil component, shown to have antimicrobial activity.
Additional notes
DefinitionChEBI: A carbobicyclic compound and sesquiterpene that is 1,2,3,4,5,6,7,8-octahydroazulene which is substituted by methyl groups at positions 1 and 4 and by a (prop-1-en-2-yl group at position 7 (the 1S,4S,7R ena tiomer).
Related reactions
2 records
Compound notes
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