Carnosol

Carnosol
Names
	IUPAC name 11,12-Dihydroxy-7β,20-epoxyabieta-8,11,13-trien-20-one
	Systematic IUPAC name (4aR,9S,10aS)-5,6-Dihydroxy-1,1-dimethyl-7-(propan-2-yl)-1,3,4,9,10,10a-hexahydro-2H-9,4a-(epoxymethano)phenanthren-12-one
Identifiers
CAS Number	5957-80-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	390568;
PubChem CID	442009;
UNII	483O455CKD ;
CompTox Dashboard (EPA)	DTXSID80904451 ;
	InChI InChI=1S/C20H26O4/c1-10(2)11-8-12-13-9-14-19(3,4)6-5-7-20(14,18(23)24-13)15(12)17(22)16(11)21/h8,10,13-14,21-22H,5-7,9H2,1-4H3/t13-,14-,20+/m0/s1 Key: XUSYGBPHQBWGAD-PJSUUKDQSA-N; InChI=1/C20H26O4/c1-10(2)11-8-12-13-9-14-19(3,4)6-5-7-20(14,18(23)24-13)15(12)17(22)16(11)21/h8,10,13-14,21-22H,5-7,9H2,1-4H3/t13-,14-,20+/m0/s1 Key: XUSYGBPHQBWGAD-PJSUUKDQBN;
	SMILES CC(C)C1=CC2=C(C(=C1O)O)[C@@]34CCCC([C@@H]3C[C@@H]2OC4=O)(C)C;
Properties
Chemical formula	C20H26O4
Molar mass	330.424 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Carnosol is a phenolic diterpene found in the herbs rosemary (Rosmarinus officinalis)^[1] and Mountain desert sage (Salvia pachyphylla).^[2]

It has been studied in-vitro for anti-cancer effects in various cancer cell types.^[3]

References

^ Ai-Hsiang Lo; Yu-Chih Liang; Shoei-Yn Lin-Shiau; Chi-Tang Ho; Jen-Kun Lin (2002). "Carnosol, an antioxidant in rosemary, suppresses inducible nitric oxide synthase through down-regulating nuclear factor-κB in mouse macrophages". Carcinogenesis. 23 (6): 983–991. doi:10.1093/carcin/23.6.983. PMID 12082020.
^ Ivan C. Guerrero; Lucia S. Andres; Leticia G. Leon; Ruben P. Machin; Jose M. Padron; Javier G. Luis; Jose Delgadillo (2006). "Abietane Diterpenoids from Salvia pachyphylla and S. clevelandii with Cytotoxic Activity against Human Cancer Cell Lines". J. Nat. Prod. 69 (12): 1803–1805. doi:10.1021/np060279i. PMID 17190465.
^ Johnson JJ (June 2011). "Carnosol: a promising anti-cancer and anti-inflammatory agent". Cancer Lett. 305 (1): 1–7. doi:10.1016/j.canlet.2011.02.005. PMC 3070765. PMID 21382660.

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Names

IUPAC name 11,12-Dihydroxy-7β,20-epoxyabieta-8,11,13-trien-20-one
Systematic IUPAC name (4aR,9S,10aS)-5,6-Dihydroxy-1,1-dimethyl-7-(propan-2-yl)-1,3,4,9,10,10a-hexahydro-2H-9,4a-(epoxymethano)phenanthren-12-one
Identifiers
CAS Number	5957-80-2^Y
3D model (JSmol)	Interactive image
ChemSpider	390568
PubChem CID	442009
UNII	483O455CKD^Y
CompTox Dashboard (EPA)	DTXSID80904451
InChI InChI=1S/C20H26O4/c1-10(2)11-8-12-13-9-14-19(3,4)6-5-7-20(14,18(23)24-13)15(12)17(22)16(11)21/h8,10,13-14,21-22H,5-7,9H2,1-4H3/t13-,14-,20+/m0/s1 Key: XUSYGBPHQBWGAD-PJSUUKDQSA-N InChI=1/C20H26O4/c1-10(2)11-8-12-13-9-14-19(3,4)6-5-7-20(14,18(23)24-13)15(12)17(22)16(11)21/h8,10,13-14,21-22H,5-7,9H2,1-4H3/t13-,14-,20+/m0/s1 Key: XUSYGBPHQBWGAD-PJSUUKDQBN
SMILES CC(C)C1=CC2=C(C(=C1O)O)[C@@]34CCCC([C@@H]3C[C@@H]2OC4=O)(C)C
Properties
Chemical formula	C₂₀H₂₆O₄
Molar mass	330.424 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references