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[2.2.1.0^2,6]hept-3-yl)-2-methylpent-2-en-1-ol
Identifiers
CAS Number	115-71-9^Y
3D model (JSmol)	Interactive image
ChemSpider	16736011
ECHA InfoCard	100.003.730
EC Number	204-102-8
KEGG	C09719
PubChem CID	5281531
UNII	15X09F2755^Y
CompTox Dashboard (EPA)	DTXSID9051587
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⁻¹
Appearance	Liquid
Density	0.9770 g/cm³
Boiling point	166 °C (331 °F; 439 K)
Solubility in water	Practically insoluble
Solubilityinethanol	Soluble
Solubilityindiethyl ether	Soluble
Chiral rotation ([α]_D)	+10.3°
Refractive index (n_D)	1.5017
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H317
Precautionary statements	P261, P272, P280, P302+P352, P321, P333+P313, P363, P501
NFPA 704 (fire 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

^ 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.

^ 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.

^ Bettenhausen, Craig (21 Nov 2020). "Making sandalwood oil without sandalwood trees". Chemical & Engineering News. Retrieved 11 Feb 2021.

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