alpha-santalol
12-alpha-santalen-14-ol
Identification
| Name | alpha-santalol |
| IUPAC | (E)-5-(2,3-dimethyl-4,5,6,7-tetrahydro-1H-tricyclo[2.2.1.02,6]heptan-3-yl)-2-methylpent-2-en-1-ol |
| CAS Number | 115-71-9 |
| EINECS | 204-102-8 |
| FDA UNII | 15X09F2755 |
| Molecular Formula | C15 H24 O |
| Molecular Weight | 220.35548000 |
| Nikkaji Number | J2.898.383B |
| CoE Number | 74 |
Regulatory
| DG SANTE Food Flavourings | 02.217 12-alpha-santalen-14-ol |
| FEMA Number | 3006 |
| FDA | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm (SATF) | 115-71-9 ; SANTALOL, ALPHA |
| FDA Regulation | FDA PART 172 -- FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION |
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.96500 to 0.97500 @ 25.00 °C. |
| Pounds per Gallon - (est). | 8.030 to 8.113 |
| Refractive Index | 1.49800 to 1.50900 @ 20.00 °C. |
| Boiling Point | 302.00 °C. @ 760.00 mm Hg, 159.00 to 160.00 °C. @ 10.00 mm Hg |
| Vapor Pressure | 0.000118 mmHg @ 25.00 °C. (est) |
| Flash Point | 281.00 °F. TCC ( 138.33 °C. ) |
| logP (o/w) | 4.530 (est) |
| Soluble in | alcohol |
| Insoluble in | water |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | perfuming agents |
Organoleptic Properties
| Odor Description | at 100.00 %. |
Safety Information
| Oral/Parenteral Toxicity | oral-rat LD50 3800 mg/kg |
| Dermal Toxicity | skin-rabbit LD50 > 5000 mg/kg |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | flavor and fragrance agents |
| RIFM Fragrance Material Safety Assessment | Search |
| maximum skin levels for fine fragrances | 0.1000 % and are based on the assumption that the fragrance mixture is used at 20% in a consumer product (IFRA Use Level Survey). (IFRA, 2004) |
| Recommendation for alpha-santalol usage levels up to | 4.0000 % in the fragrance concentrate. |
| use level in formulae for use in cosmetics | 0.1500 % |
| Dermal Systemic Exposure in Cosmetic Products | 0.0038 mg/kg/day (IFRA, 2004) |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 0.11 (μg/capita/day) |
| Modified Theoretical Added Maximum Daily Intake (mTAMDI) | 3900 (μg/person/day) |
| Threshold of Concern | 1800 (μg/person/day) |
| Structure Class | I |
| baked goods | 1.00000 |
| beverages(nonalcoholic) | 0.06000 |
| beverages(alcoholic) | - |
| breakfast cereal | - |
| cheese | - |
| chewing gum | - |
| condiments / relishes | - |
| confectionery froastings | - |
| egg products | - |
| fats / oils | - |
| fish products | - |
| frozen dairy | 0.35000 |
| fruit ices | 0.35000 |
| gelatins / puddings | - |
| granulated sugar | - |
| gravies | - |
| hard candy | 1.00000 |
| 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 | - |
| Dairy products, excluding products of category 02.0 (01.0) | 7.00000 |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0) | 5.00000 |
| Edible ices, including sherbet and sorbet (03.0) | 10.00000 |
| Processed fruit (04.1) | 7.00000 |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2) | - |
| Confectionery (05.0) | 10.00000 |
| Chewing gum (05.3) | - |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0) | 5.00000 |
| Bakery wares (07.0) | 10.00000 |
| Meat and meat products, including poultry and game (08.0) | 2.00000 |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0) | 2.00000 |
| Eggs and egg products (10.0) | 2.00000 |
| Sweeteners, including honey (11.0) | 2.00000 |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0) | 5.00000 |
| Foodstuffs intended for particular nutritional uses (13.0) | 10.00000 |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1) | 5.00000 |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2) | 10.00000 |
| Ready-to-eat savouries (15.0) | 20.00000 |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0) | 5.00000 |
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Potential Uses
Natural Occurrence
Synonyms
alpha-
argeol
arheol
(Z)-alpha-5-(2,3-
dimethyl tricyclo(2.2.1.0(2,6))hept-3-yl)-2-methyl-2-penten-1-ol
(Z)-alpha-5-(2,3-
dimethyl tricyclo(2.2.1.02,6)hept-3-yl)-2-methyl-2-penten-1-ol stereoisomer
12-alpha-
santalen-14-ol
(Z)-alpha-
santalol
cis-alpha-
santalol
PubMed:
Relationship Between Emotional Behavior in Mice and the Concentration of (+)-α-Santalol in the Brain.
PubMed:
Suppression of lipopolysaccharide-stimulated cytokine/chemokine production in skin cells by sandalwood oils and purified α-santalol and β-santalol.
PubMed:
Biocatalyst mediated regio- and stereo-selective hydroxylation and epoxidation of (Z)-α-santalol.
PubMed:
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.
PubMed:
α-Santalol, a skin cancer chemopreventive agent with potential to target various pathways involved in photocarcinogenesis.
PubMed:
Chemopreventive effects of combination of honokiol and magnolol with α-santalol on skin cancer developments.
PubMed:
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.
PubMed:
Structural factors in the odor of alpha-santalol derivatives.
PubMed:
Evaluation of in vivo anti-hyperglycemic and antioxidant potentials of α-santalol and sandalwood oil.
PubMed:
α-Santalol, a derivative of sandalwood oil, induces apoptosis in human prostate cancer cells by causing caspase-3 activation.
PubMed:
Structure-odor relationships of α-santalol derivatives with modified side chains.
PubMed:
α-Santalol derivatives from Santalum album and their cytotoxic activities.
PubMed:
Determination of the absolute stereochemistry of limonene and alpha-santalol by Raman optical activity spectroscopy.
PubMed:
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.
PubMed:
Skin cancer chemoprevention by α-santalol.
PubMed:
Molecular regulation of santalol biosynthesis in Santalum album L.
PubMed:
endo/exo stereoselectivity in Diels-Alder reactions of α,β-dialkylated conjugated enals to cyclic 1,3-dienes: intermediates in the synthesis of (-)-β-santalol and its analogs.
PubMed:
Repellent effect of santalol from sandalwood oil against Tetranychus urticae (Acari: Tetranychidae).
PubMed:
Structure-odor relationships of semisynthetic β-santalol analogs.
PubMed:
Anticancer Effects of Sandalwood (Santalum album).
PubMed:
Acaricidal and oviposition deterring effects of santalol identified in sandalwood oil against two-spotted spider mite, Tetranychus urticae Koch (Acari: Tetranychidae).
PubMed:
In vitro anti-viral effect of β-santalol against influenza viral replication.
PubMed:
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.
PubMed:
A rare type of sesquiterpene and β-santalol derivatives from Santalum album and their cytotoxic activities.
PubMed:
Chemoprevention by alpha-santalol on UVB radiation-induced skin tumor development in mice.
PubMed:
Effects of alpha-santalol on proapoptotic caspases and p53 expression in UVB irradiated mouse skin.
PubMed:
Chemopreventive effects of various concentrations of alpha-santalol on skin cancer development in CD-1 mice.
PubMed:
Chemopreventive effects of alpha-santalol on ultraviolet B radiation-induced skin tumor development in SKH-1 hairless mice.
PubMed:
Chemopreventive effects of alpha-santalol on skin tumor development in CD-1 and SENCAR mice.
PubMed:
A novel chemopreventive mechanism for a traditional medicine: East Indian sandalwood oil induces autophagy and cell death in proliferating keratinocytes.
PubMed:
East Indian Sandalwood and alpha-santalol odor increase physiological and self-rated arousal in humans.
PubMed:
The transcriptome of sesquiterpenoid biosynthesis in heartwood xylem of Western Australian sandalwood (Santalum spicatum).
PubMed:
Fragrance material review on alpha-santalol.
PubMed:
Evaluation of the effects of East Indian sandalwood oil and alpha-santalol on humans after transdermal absorption.
PubMed:
Hawaiian sandalwood: oil composition of Santalum paniculatum and comparison with other sandal species.
PubMed:
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.
PubMed:
TLC-bioautographic evaluation of in vitro anti-tyrosinase and anti-cholinesterase potentials of sandalwood oil.
PubMed:
Effect of α-santalol and β-santalol from sandalwood on the central nervous system in mice.
PubMed:
(13)C-NMR spectra of santalol derivatives: a comparison of DFT-based calculations and database-oriented prediction techniques.
PubMed:
The synthesis of (Z)-trisubstituted allylic alcohols by the selective 1,4-hydrogenation of dienol esters: improved synthesis of (-)-β-santalol.
PubMed:
Effects of sesquiterpenoids from "Oriental incenses" on acetic acid-induced writhing and D2 and 5-HT2A receptors in rat brain.
PubMed:
Geographic and phenotypic variation in heartwood and essential-oil characters in natural populations of Santalum austrocaledonicum in Vanuatu.
PubMed:
[Effect of santalol on the sleep-wake cycle in sleep-disturbed rats].
PubMed:
Fragrance material review on santalol.
PubMed:
Structure-activity relationships of sandalwood odorants: synthesis and odour of methyl-beta-santalol.
PubMed:
Syntheses and odor of "bulky group"-modified sandalwood odorants: isophorono-beta-santalol analogues.
PubMed:
Structure-activity relationships of sandalwood odorants: total synthesis and fragrance properties of cyclopropano-beta-santalol.
PubMed:
Synthesis and olfactoric activity of side-chain modified beta-santalol analogues.
PubMed:
Enantioselective synthesis of (-)-beta-santalol by a copper-catalyzed enynol cyclization-fragmentation reaction.
PubMed:
Antimicrobial activity and chemical composition of endemic Centaurea cariensis subsp. niveo-tomentosa.
PubMed:
[Preparation of santalol by centrifugal-thin layer chromatographic method].
PubMed:
Structure-activity relationships of sandalwood odorants: synthesis and odor of tricyclo beta-santalol.
PubMed:
Biosynthesis of Sandalwood Oil: Santalum album CYP76F cytochromes P450 produce santalols and bergamotol.
PubMed:
Chemical composition of the essential oils of Clausena lansium from Hainan Island, China.
PubMed:
Chemical composition of volatile oils from the pericarps of Indian sandalwood (Santalum album) by different extraction methods.
PubMed:
α- and β-Santalols Directly Interact with Tubulin and Cause Mitotic Arrest and Cytotoxicity in Oral Cancer Cells.
PubMed:
Transcriptional upregulation of Nrf2-dependent phase II detoxification genes in the involved epidermis of vitiligo vulgaris.
PubMed:
Anti-Helicobacter pylori compounds from Santalum album.
PubMed:
In the quest for a virtual pseudo receptor for sandalwood-like odorants. Part I: The empirical approach.
PubMed:
Comprehensive two-dimensional gas chromatography with flame ionization and time-of-flight mass spectrometry detection: qualitative and quantitative analysis of West Australian sandalwood oil.
PubMed:
Evaluation of the quality of sandalwood essential oils by gas chromatography-mass spectrometry.
PubMed:
Analysis of fragrance compounds in blood samples of mice by gas chromatography, mass spectrometry, GC/FTIR and GC/AES after inhalation of sandalwood oil.
PubMed:
Biotransformation of terpenoids by mammals, microorganisms, and plant-cultured cells.
PubMed:
Safety assessment of sandalwood oil (Santalum album L.).
PubMed:
Synthesis of new exo- and endo-3,8-dihydro-beta-santalols and other norbornyl-derived alcohols.
PubMed:
Comparative phytochemical analysis and antibacterial efficacy of in vitro and in vivo extracts from East Indian sandalwood tree (Santalum album L.).
PubMed:
Application of a multidimensional gas chromatography system with simultaneous mass spectrometric and flame ionization detection to the analysis of sandalwood oil.
PubMed:
Structure-activity relationships of sandalwood odorants: synthesis of a new campholene derivative.
PubMed:
Synthesis and olfactory evaluation of bulky moiety-modified analogues to the sandalwood odorant Polysantol.
PubMed:
[The influence of external stimulation on content and quality of volatile oil in Lignun Santali albi].
PubMed:
6-Substituted indanoyl isoleucine conjugate induces tobacco plant responses in secondary metabolites.
PubMed:
Essential oil composition of three Peperomia species from the Amazon, Brazil.
PubMed:
Recent developments in the chemistry of sandalwood odorants.
PubMed:
Depigmented contact dermatitis due to incense.
PubMed:
Comparative molecular and phytochemical study of the tree species Santalum austrocaledonicum (Santalaceae) distributed in the New-Caledonian archipelago.
PubMed:
Composition, antimicrobial activity and cytotoxicity of essential oils from Aristolochia mollissima.
PubMed:
Broad activation of the glomerular layer enhances subsequent olfactory responses.
PubMed:
Microbiological transformations of terpenes. III. Transformations of some mono- and sesqui-terpenes.