10298. Carnosol

Nomenclature

CAS number: 5957-80-2
(4aR,9S,10aS)-1,3,4,9,10,10a-Hexahydro-5,6-dihydroxy-1,1-dimethyl-7-(1-methylethyl)-2H-9,4a-(epoxymethano)phenanthren-12-one; 7β,11,12-trihydroxy-13-isopropylpodocarpa-8,11,13-trien-17-oic acid 17,7-lactone; picrosalvin.
C20H26O4; mol wt 330.42.
C 72.70%, H 7.93%, O 19.37%.

Description and references

Phenolic diterpene antioxidant principally occurring in rosemary and sage; lactone of carnosic acid, q.v. Isoln from Salvia carnosa, Dougl., Lamiaceae: A. I. White, G. L. Jenkins, J. Am. Pharm. Assoc. 31, 33, 37 (1942). Isoln as picrosalvin from S. officinalis, L.: C. H. Brieskorn, A. Fuchs, Ber. 95, 3034 (1962) DOI. Isoln from rosemary and identity with picrosalvin: idem et al., J. Org. Chem. 29, 2293 (1964) DOI. Prepn by oxidation of carnosic acid: J. G. Marrero et al., J. Nat. Prod. 65, 986 (2002) DOI PubMed. Crystal structure and spectroscopic properties: M. Gajhede et al., J. Crystallogr. Spectrosc. Res. 20, 165 (1990) DOI. Antioxidant activity in lipids: C. H. Brieskorn, H.-J. Dmling, Z. Lebensm.-Unters. Forsch. 141, 1431 (1969) DOI; in biological systems: O. I. Aruoma et al., Xenobiotica 22, 257 (1992) PubMed; in oil-in-water emulsion: E. N. Frankel et al., J. Agric. Food Chem. 44, 131 (1996) DOI. Anticancer effects in murine model of colonic tumorigenesis: A. E. Moran et al., Cancer Res. 65, 1097 (2005) PubMed.

Chemical structure

Properties

Long, white, odorless needles, mp 219.5° (dec) (White, Jenkins). Also reported as mp 221-226° (Brieskorn, Fuchs). Intensely bitter taste. [α]D 66°. uv max (ethanol): 210, 284 nm (log ε 4.42, 3.40). Soly (mg/ml): 8 in ethanol, 35 in DMF, 250 in DMSO. Sol in methanol, ether, chloroform; slightly sol in petr ether. Sol in dil alkali with red-brown color.

Use

Antioxidant in edible oils, meats, and other fat containing foods.