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α-Santalol

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(Redirected from Alpha santalol) Chemical compound
α-Santalol
Names
IUPAC name (Z)-5-(2,3-Dimethyltricyclolhept-3-yl)-2-methylpent-2-en-1-ol
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.730 Edit this at Wikidata
EC Number
  • 204-102-8
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C15H24O/c1-10(9-16)5-4-6-14(2)11-7-12-13(8-11)15(12,14)3/h5,11-13,16H,4,6-9H2,1-3H3/b10-5-Key: PDEQKAVEYSOLJX-YHYXMXQVSA-N
SMILES
  • C/C(CO)=C\CCC3(C)C1CC2C(C1)C23C
Properties
Chemical formula C15H24O
Molar mass 220.356 g·mol
Appearance Liquid
Density 0.9770 g/cm
Boiling point 166 °C (331 °F; 439 K)
Solubility in water Practically insoluble
Solubility in ethanol Soluble
Solubility in diethyl ether Soluble
Chiral rotation (D) +10.3°
Refractive index (nD) 1.5017
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H317
Precautionary statements P261, P272, P280, P302+P352, P321, P333+P313, P363, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0 1 0
Related compounds
Related terpenes β-Santalol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

α-Santalol (alpha-santalol) is an organic compound that is classified as a sesquiterpene. It comprises about 55% of the oil of sandalwood, another less abundant component being β-santalol. As of 2002, about 60 tons of sandalwood oil are produced annually by steam distillation of the heartwood of Santalum album. It is a valued component for perfumes.

Because of concerns about the sustainability of sandalwood tree cultivation, scientists have developed routes to α-santalol and β-santalol via fermentation, including using Rhodobacter sphaeroides. BASF launched its version, Isiobionic Santalol, in July 2020.

The oil content varies greatly within the different sandalwood species. This level is typically highest in S. album, S. paniculatum and S. yasi. The scent profile also changes considerably between the different species' oils.

References

  1. Bommareddy, A; Brozena, S; Steigerwalt, J; et al. (2019). "Medicinal properties of alpha-santalol, a naturally occurring constituent of sandalwood oil: review". Nat. Prod. Res. 33 (4): 527–543. doi:10.1080/14786419.2017.1399387. PMID 29130352. S2CID 27852488.
  2. Karl-Georg Fahlbusch; Franz-Josef Hammerschmidt; Johannes Panten; Wilhelm Pickenhagen; Dietmar Schatkowski; Kurt Bauer; Dorothea Garbe; Horst Surburg (2002). "Flavors and Fragrances". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a11_141. ISBN 3527306730.
  3. Bettenhausen, Craig (21 Nov 2020). "Making sandalwood oil without sandalwood trees". Chemical & Engineering News. Retrieved 11 Feb 2021.


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