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General Material Information

Preferred name (-)-guaiol
Trivial Name 2-[(3R,5S,8R)-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl]propan-2-ol
Short Description guai-1(5)-en-11-ol
Formula C15 H26 O
CAS Number 489-86-1
CAS Number 489-86-1 (SRS)
ECHA Number 207-702-8
FDA UNII I7WP008A91
Nikkaji Number J74.702E
Beilstein Number 2047993
MDL MFCD00043336
xLogP3-AA 3.10 (est)
Bio Activity Summary External link
NMR Predictor External link
Synonyms
  • 5-azulenemethanol, 1,2,3,4,5,6,7,8-octahydro-a,a,3,8-tetramethyl-, (3S,5R,8S)-
  • 5-azulenemethanol, 1,2,3,4,5,6,7,8-octahydro-a,a,3,8-tetramethyl-, [3S-(3a,5a,8a)]-
  • champaca camphor
  • champacol
  • 2-[(3R,5S,8R)-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl]propan-2-ol
  • guai-1(5)-en-11-ol
  • guaiac alcohol
  • (-)- guaiol
  • octahydro-3,8-dimethyl azulen-5-yl propan-2-ol
  • 2-((3S,8S)-1,2,3,4,5,6,7,8-octahydro-3,8-dimethyl azulen-5-yl) propan-2-ol
  • 2-((3S,8S)-1,2,3,4,5,6,7,8-octahydro-3,8-dimethylazulen-5-yl)propan-2-ol
  • (3S-(3alpha, 5alpha,8alpha))- 1,2,3,4,5,6,7,8-octahydro-alpha,alpha,3,8-tetramethyl-5-azulenemethanol

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Literature & References

2-[(3R,5S,8R)-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl]propan-2-ol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:489-86-1
Pubchem (cid):72607
Pubchem (sid):135030157
Flavornet:489-86-1
Pherobase:View
2-[(3S,5R,8S)-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl]propan-2-ol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:489-86-1
Pubchem (cid):227829
Pubchem (sid):82678
Publications by PubMed
Guaiol--a naturally occurring insecticidal sesquiterpene.
Essential oil compositions of Alphonsea philastreana (Pierre) Pierre ex Finet & Gagnep. and Alphonsea gaudichaudiana (Baill.) Finet & Gagnep. from Vietnam.
Chemotaxonomic importance of the essential-oil composition in two subspecies of Teucrium stocksianum Boiss. from Iran.
Antifungal Activity of the Essential Oils of Callitris neocaledonica and C. sulcata Heartwood (Cupressaceae).
Chemical diversity in the essential oil of Indian valerian (Valeriana jatamansi Jones).
Acaricidal activity against Tetranychus urticae and essential oil composition of four Croton species from Caatinga biome in northeastern Brazil.
Analysis of the essential oil of Amsonia illustris.
Phytochemical analysis and in vitro free-radical-scavenging activities of the essential oils from leaf and fruit of Melaleuca leucadendra L.
Anti-inflammatory activity of essential oil from leaves of Myrciaria tenella and Calycorectes sellowianus.
[GC-MS analysis of volatile constituents from five different kinds of Chinese eaglewood].
Muscodor albus E-6, an endophyte of Guazuma ulmifolia making volatile antibiotics: isolation, characterization and experimental establishment in the host plant.
Microbial transformation of (-)-guaiol and antibacterial activity of its transformed products.
Efficacy of botanical extracts from Callitris glaucophylla, against Aedes aegypti and Culex annulirostris mosquitoes.
Two new bioactive sesquiterpenes from the soft coral Sinularia sp.
Biotransformation of (-)-guaiol by Eurotium rubrum as a biocatalyst.
Analysis of the essential oils of the leaves, stems, rhizomes and roots of the medicinal plant Alpinia galanga from southern India.
Torilin from Torilis japonica, as a new inhibitor of testosterone 5 alpha-reductase.
[Analysis of chemical constituents in the essential oil from roots of Litsea rotundifolia var. oblongifolia by GC/MS].
[Analysis of chemical constituents in the essential oil from Evodia fargesii by GC/MS].
The guaiol color reaction.
A novel phenanthrenolide and C-benzyl dihydrochalcones from Uvaria puguensis.
Quinoline alkaloids, coumarins and volatile constituents of Helietta longifoliata.
GLC-mass spectrometry of Teucrium polium oil.
Studies on seven-membered ring derivatives. IV. 6,10-Dimethylbicyclo-[5.3.0]decanones obtained from guaiol.

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C09676
HMDB (The Human Metabolome Database):Search
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 222.37141418457
Melting Point 91 to 93°C @ 760 mm Hg
Boiling Point 309 to 310°C @ 760 mm Hg
Vapor Pressure 5.4E-5 mmHg @ 25 °C
Flash Point TCC Value 113.33 °C TCC
logP (o/w) 4.782 est
Shelf life 12 months (or longer if stored properly.)
Storage notes Refrigerate in tightly sealed containers.
Solubility
alcohol Yes
water, 3.61 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Woody
guaiacwood, rose tea rose, woody
Luebke, William tgsc, (1987) At 100.00 %. mild guaiacwood tea rose

Occurrences

Potential Uses

Applications
Odor purposes Amber, Balsam, Guaiacwood, Moss, Oriental, Rose tea rose, Woody
Flavoring purposes Guaiacwood
Cosmetic purposes Perfuming agents

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
None - None found.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for (-)-guaiol usage levels up to:
5.0000 % in the fragrance concentrate.
Recommendation for (-)-guaiol flavor usage levels up to:
not for flavor use.

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):489-86-1
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :72607
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2-[(3R,5S,8R)-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl]propan-2-ol
Chemidplus:0000489861
2-[(3S,5R,8S)-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl]propan-2-ol