α-Santalol

α-Santalol, also referred to as alpha-santalol,[1] 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.[2]

α-Santalol
Names
IUPAC name
(Z)-5-(2,3-Dimethyltricyclol[2.2.1.02,6]hept-3-yl)-2-methylpent-2-en-1-ol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.730
EC Number
  • 204-102-8
KEGG
UNII
  • 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
  • C/C(CO)=C\CCC3(C)C1CC2C(C1)C23C
Properties
C15H24O
Molar mass 220.356 g·mol−1
Appearance Liquid
Density 0.9770 g/cm3
Boiling point 166 °C (331 °F; 439 K)
Practically insoluble
Solubility in ethanol Soluble
Solubility in diethyl ether Soluble
+10.3°
1.5017
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H317
P261, P272, P280, P302+P352, P321, P333+P313, P363, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
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 [77 °F], 100 kPa).
Infobox references

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.[3]

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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