Achilleol A

Achilleol A
Names
	IUPAC name (1S,3R)-2,2-dimethyl-4-methylidene-3-[(3E,7E,11E)-3,8,12,16-tetramethylheptadeca-3,7,11,15-tetraenyl]cyclohexan-1-ol
Identifiers
CAS Number	125287-06-1;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:189410;
ChEMBL	ChEMBL1977780;
ChemSpider	4581493;
PubChem CID	5471312;
	InChI InChI=1S/C30H50O/c1-23(2)13-11-16-25(4)18-12-17-24(3)14-9-10-15-26(5)19-21-28-27(6)20-22-29(31)30(28,7)8/h13-15,18,28-29,31H,6,9-12,16-17,19-22H2,1-5,7-8H3/b24-14+,25-18+,26-15+/t28-,29+/m1/s1 Key: ANKPMKKGZZQDIC-HJSIMFEZSA-N;
	SMILES CC(=CCC/C(=C/CC/C(=C/CC/C=C(\C)/CC[C@@H]1C(=C)CC[C@@H](C1(C)C)O)/C)/C)C;
Properties
Chemical formula	C30H50O
Molar mass	426.729 g·mol−1
Density	g/cm3
Melting point	116 °C
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Achilleol A is a monocyclic triterpene with the molecular formula C₃₀H₅₀O.^[1]

Natural occurrence

The compound is found in such taxons as Achillea odorata,^[2]^[3] Camellia oleifera, Santolina elegans, Triticum aestivum, among others.

Synthesis

There is a simple method for synthesizing the monocyclic triterpene achilleol A, employing titanium(III) chemistry as the crucial step. This synthesis validates the structure previously determined by spectroscopic analysis.^[4]

References

^ Barrero, A.F.; Alvarez-Manzaneda, E.J.R.; Alvarez-Manzaneda r, R. (1989-01-01). "Achilleol A: A new monocyclic triterpene skeleton from Achillea odorata L.". Tetrahedron Letters. 30 (25): 3351–3352. doi:10.1016/S0040-4039(00)99242-6. ISSN 0040-4039.
^ Daniel, M.; Mammen, Denni (1 June 2016). Analytical Methods for Medicinal Plants and Economic Botany. Scientific Publishers. p. 114. ISBN 978-93-87307-58-2. Retrieved 22 July 2025.
^ Keinan, Ehud (6 March 2006). Catalytic Antibodies. John Wiley & Sons. p. 201. ISBN 978-3-527-60505-7. Retrieved 22 July 2025.
^ Barrero, Alejandro F; Cuerva, Juan M; Alvarez-Manzaneda, E. J; Oltra, J. Enrique; Chahboun, Rachid (8 April 2002). "First synthesis of achilleol A using titanium(III) chemistry". Tetrahedron Letters. 43 (15): 2793–2796. doi:10.1016/S0040-4039(02)00358-1. ISSN 0040-4039. Retrieved 22 July 2025.

[1] Barrero, A.F.; Alvarez-Manzaneda, E.J.R.; Alvarez-Manzaneda r, R. (1989-01-01). "Achilleol A: A new monocyclic triterpene skeleton from Achillea odorata L.". Tetrahedron Letters. 30 (25): 3351–3352. doi:10.1016/S0040-4039(00)99242-6. ISSN 0040-4039.

[2] Daniel, M.; Mammen, Denni (1 June 2016). Analytical Methods for Medicinal Plants and Economic Botany. Scientific Publishers. p. 114. ISBN 978-93-87307-58-2. Retrieved 22 July 2025.

[3] Keinan, Ehud (6 March 2006). Catalytic Antibodies. John Wiley & Sons. p. 201. ISBN 978-3-527-60505-7. Retrieved 22 July 2025.

[4] Barrero, Alejandro F; Cuerva, Juan M; Alvarez-Manzaneda, E. J; Oltra, J. Enrique; Chahboun, Rachid (8 April 2002). "First synthesis of achilleol A using titanium(III) chemistry". Tetrahedron Letters. 43 (15): 2793–2796. doi:10.1016/S0040-4039(02)00358-1. ISSN 0040-4039. Retrieved 22 July 2025.

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