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santalol

Chemical Structure

General Material Information

Preferred name santalol
Trivial Name Santalol
Short Description santalol (alpha & beta)
Formula C15 H24 O
CAS Number 11031-45-1
FEMA Number 3006
ECHA Number 234-262-4
FDA UNII 1DGG9VW8SA
MDL MFCD00046301
COE Number 74
xLogP3-AA 4.60 (est)
NMR Predictor External link
JECFA Food Flavoring 984 santalol (alpha & beta)
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 11031-45-1 ; SANTALOL (ALPHA AND BETA)
Synonyms
  • alpha,beta- argeol
  • artheol
  • 5-(2,3-dimethyl tricyclo(2.2.1.0(2,6))hept-3-yl)-2-methyl-2-penten-1-ol
  • (7E,9E,11E,13E)- pentadeca-7,9,11,13-tetraen-1-ol
  • alpha,beta- santalol
  • santalol (alpha & beta)
  • santalol nat australia (Robertet)
  • (7E,9E,11E,13E)-pentadeca-7,9,11,13-tetraen-1-ol

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

(7E,9E,11E,13E)-pentadeca-7,9,11,13-tetraen-1-ol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:11031-45-1
Pubchem (cid):24832101
Pubchem (sid):135018040
Publications by PubMed
Biocatalyst mediated regio- and stereo-selective hydroxylation and epoxidation of (Z)-α-santalol.
Biosynthesis of Sandalwood Oil: Santalum album CYP76F cytochromes P450 produce santalols and bergamotol.
Suppression of Lipopolysaccharide-stimulated Cytokine/Chemokine Production in Skin Cells by Sandalwood Oils and Purified α-santalol and β-santalol.
α-santalol inhibits the angiogenesis and growth of human prostate tumor growth by targeting vascular endothelial growth factor receptor 2-mediated AKT/mTOR/P70S6K signaling pathway.
Structural factors in the odor of alpha-santalol derivatives.
Chemopreventive effects of combination of honokiol and magnolol with α-santalol on skin cancer developments.
Molecular regulation of santalol biosynthesis in Santalum album L.
TLC-bioautographic evaluation of in vitro anti-tyrosinase and anti-cholinesterase potentials of sandalwood oil.
α-Santalol, a skin cancer chemopreventive agent with potential to target various pathways involved in photocarcinogenesis.
Antineoplastic effects of α-santalol on estrogen receptor-positive and estrogen receptor-negative breast cancer cells through cell cycle arrest at G2/M phase and induction of apoptosis.
Evaluation of in vivo anti-hyperglycemic and antioxidant potentials of α-santalol and sandalwood oil.
Preparative separation of α- and β-santalenes and (Z)-α- and (Z)-β-santalols using silver nitrate-impregnated silica gel medium pressure liquid chromatography and analysis of sandalwood oil.
Repellent effect of santalol from sandalwood oil against Tetranychus urticae (Acari: Tetranychidae).
Determination of the absolute stereochemistry of limonene and alpha-santalol by Raman optical activity spectroscopy.
α-Santalol, a derivative of sandalwood oil, induces apoptosis in human prostate cancer cells by causing caspase-3 activation.
Chemical composition of volatile oils from the pericarps of Indian sandalwood (Santalum album) by different extraction methods.
α-Santalol derivatives from Santalum album and their cytotoxic activities.
Structure-odor relationships of α-santalol derivatives with modified side chains.
In vitro anti-viral effect of β-santalol against influenza viral replication.
Acaricidal and oviposition deterring effects of santalol identified in sandalwood oil against two-spotted spider mite, Tetranychus urticae Koch (Acari: Tetranychidae).
The synthesis of (Z)-trisubstituted allylic alcohols by the selective 1,4-hydrogenation of dienol esters: improved synthesis of (-)-β-santalol.
Skin cancer chemoprevention by α-santalol.
Application of a multidimensional gas chromatography system with simultaneous mass spectrometric and flame ionization detection to the analysis of sandalwood oil.
Structure-activity relationships of sandalwood odorants: synthesis of a new campholene derivative.
Geographic and phenotypic variation in heartwood and essential-oil characters in natural populations of Santalum austrocaledonicum in Vanuatu.
Alpha-santalol, a chemopreventive agent against skin cancer, causes G2/M cell cycle arrest in both p53-mutated human epidermoid carcinoma A431 cells and p53 wild-type human melanoma UACC-62 cells.
Transcriptional upregulation of Nrf2-dependent phase II detoxification genes in the involved epidermis of vitiligo vulgaris.
Antimicrobial activity and chemical composition of endemic Centaurea cariensis subsp. niveo-tomentosa.
Synthesis of new exo- and endo-3,8-dihydro-beta-santalols and other norbornyl-derived alcohols.
Enantioselective synthesis of (-)-beta-santalol by a copper-catalyzed enynol cyclization-fragmentation reaction.
Synthesis and olfactory evaluation of bulky moiety-modified analogues to the sandalwood odorant Polysantol.
(13)C-NMR spectra of santalol derivatives: a comparison of DFT-based calculations and database-oriented prediction techniques.
Essential oil composition of three Peperomia species from the Amazon, Brazil.
Fragrance material review on alpha-santalol.
Fragrance material review on santalol.
Recent developments in the chemistry of sandalwood odorants.
Effects of alpha-santalol on proapoptotic caspases and p53 expression in UVB irradiated mouse skin.
Structure-activity relationships of sandalwood odorants: total synthesis and fragrance properties of cyclopropano-beta-santalol.
Safety assessment of sandalwood oil (Santalum album L.).
[Effect of santalol on the sleep-wake cycle in sleep-disturbed rats].
Chemoprevention by alpha-santalol on UVB radiation-induced skin tumor development in mice.
Comparative molecular and phytochemical study of the tree species Santalum austrocaledonicum (Santalaceae) distributed in the New-Caledonian archipelago.
Composition, antimicrobial activity and cytotoxicity of essential oils from Aristolochia mollissima.
Biotransformation of terpenoids by mammals, microorganisms, and plant-cultured cells.
In the quest for a virtual pseudo receptor for sandalwood-like odorants. Part I: The empirical approach.
Broad activation of the glomerular layer enhances subsequent olfactory responses.
East Indian Sandalwood and alpha-santalol odor increase physiological and self-rated arousal in humans.
Chemopreventive effects of alpha-santalol on ultraviolet B radiation-induced skin tumor development in SKH-1 hairless mice.
Syntheses and odor of "bulky group"-modified sandalwood odorants: isophorono-beta-santalol analogues.
Chemopreventive effects of various concentrations of alpha-santalol on skin cancer development in CD-1 mice.
Anti-Helicobacter pylori compounds from Santalum album.
6-Substituted indanoyl isoleucine conjugate induces tobacco plant responses in secondary metabolites.
Structure-activity relationships of sandalwood odorants: synthesis and odor of tricyclo beta-santalol.
Skin cancer chemopreventive agent, {alpha}-santalol, induces apoptotic death of human epidermoid carcinoma A431 cells via caspase activation together with dissipation of mitochondrial membrane potential and cytochrome c release.
Comprehensive two-dimensional gas chromatography with flame ionization and time-of-flight mass spectrometry detection: qualitative and quantitative analysis of West Australian sandalwood oil.
Chemical composition of the essential oils of Clausena lansium from Hainan Island, China.
Evaluation of the quality of sandalwood essential oils by gas chromatography-mass spectrometry.
Evaluation of the effects of East Indian sandalwood oil and alpha-santalol on humans after transdermal absorption.
Chemopreventive effects of alpha-santalol on skin tumor development in CD-1 and SENCAR mice.
[The influence of external stimulation on content and quality of volatile oil in Lignun Santali albi].
Synthesis and olfactoric activity of side-chain modified beta-santalol analogues.
Effects of sesquiterpenoids from "Oriental incenses" on acetic acid-induced writhing and D2 and 5-HT2A receptors in rat brain.
Structure-activity relationships of sandalwood odorants: synthesis and odour of methyl-beta-santalol.
Effect of α-santalol and β-santalol from sandalwood on the central nervous system in mice.
Analysis of fragrance compounds in blood samples of mice by gas chromatography, mass spectrometry, GC/FTIR and GC/AES after inhalation of sandalwood oil.
Depigmented contact dermatitis due to incense.
[Preparation of santalol by centrifugal-thin layer chromatographic method].
Microbiological transformations of terpenes. III. Transformations of some mono- and sesqui-terpenes.

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
FDA Substances Added to Food (formerly EAFUS):View
HMDB (The Human Metabolome Database):Search
FooDB:FDB010229
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex Yes
Molecular weight 220.35548400879
Specific gravity @ 20 °C
Pounds per Gallon 8.072 to 8.139
Boiling Point 101 to 103°C @ 0.1 mm Hg
Vapor Pressure 2.0E-6 mmHg @ 25 °C
Flash Point TCC Value 100 °C TCC
logP (o/w) 4.647 est
Shelf life 24 months (or longer if stored properly.)
Storage notes Store in cool, dry place in tightly sealed containers, protected from heat and light.
Solubility
alcohol Yes
fixed oils Yes
propylene glycol Yes
water, 4.188 mg/L @ 25 °C (est) Yes
glycerin No
Stability
cream Unspecified
hair spray Unspecified
lotion Unspecified
non-discoloring in most media Unspecified
powder Unspecified
soap Unspecified

Organoleptic Properties

Odor Type: Woody
sweet, sandalwood, woody
Luebke, William tgsc, (1991) At 100.00 %. deep sweet sandalwood woody

Occurrences

Potential Uses

Applications
Odor purposes Amber, Animal, Balsam, Floral, Moss, Musk, Oriental, Sandalwood, Woody
Cosmetic purposes Perfuming agents

Safety Information

Safety information

European information :
Most important hazard(s):
Xi - Irritant
R 36/38 - Irritating to skin and eyes.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36 - Wear suitable protective clothing.
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.
Human Experience:
20 % solution: no irritation or sensitization.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and 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 santalol usage levels up to:
8.0000 % in the fragrance concentrate.
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 3
Click here to view publication 3
average usual ppmaverage maximum ppm
baked goods: 1.000008.00000
beverages(nonalcoholic): 0.060002.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: -0.20000
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: 0.350002.00000
fruit ices: 0.350002.00000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: 1.0000010.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):11031-45-1
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :24832101
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
(7E,9E,11E,13E)-pentadeca-7,9,11,13-tetraen-1-ol
Chemidplus:0011031451