| Identification | Back Directory | [Name]
CARNOSOL | [CAS]
5957-80-2 | [Synonyms]
CARNOSOL
CARNOSOL(RG)
CARNOSOL USP/EP/BP
Carnosol, froM RoseMarinus officinalis
Carnosol, 98%, from Rosemarinus officinalis
1,3,4,9,10AS-HEXAHYDRO-5,6-DIHYDROXY-1,1-DIMETHYL-7-ISO-PROPYL-2H-9S,4AR-(EPOXYMETHANO)PHENANTHREN-12-ONE
1,3,4,9,10,10AS-HEXAHYDRO-5,6-DIHYDROXY-1,1-DIMETHYL-7-ISO-PROPYL-2H-9S,4AR-(EPOXYMETHANO)PHENANTHREN-12-ONE
1,2,3,4,4A,9,10,10AS-OCTAHYDRO-5,6-DIHYDROXY-1,1-DIMETHYL-7-ISOPROPYL-9S, 4AR (EPOXYMETHANO)PHENANTHREN-12-ONE
2H-9,4a-(Epoxymethano)phenanthren-12-one, 1,3,4,9,10,10a-hexahydro-5,6-dihydroxy-1,1-dimethyl-7-(1-methylethyl)-, (4aR,9S,10aS)- | [Molecular Formula]
C20H26O4 | [MDL Number]
MFCD02752467 | [MOL File]
5957-80-2.mol | [Molecular Weight]
330.42 |
| Chemical Properties | Back Directory | [Melting point ]
240～242℃ | [Boiling point ]
524.8±50.0 °C(Predicted) | [density ]
1.26±0.1 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Store in freezer, under -20°C | [solubility ]
DMSO:66.0(Max Conc. mg/mL);199.74(Max Conc. mM) | [form ]
neat | [pka]
8.91±0.40(Predicted) | [color ]
White | [biological source]
Rosemarinus officinalis L. leaves | [Major Application]
food and beverages | [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 | [InChIKey]
XUSYGBPHQBWGAD-PJSUUKDQSA-N | [SMILES]
C1(C)(C)[C@@]2([H])[C@]3(C(=O)O[C@@]([H])(C2)C2=C3C(O)=C(O)C(C(C)C)=C2)CCC1 | [LogP]
2.832 (est) |
| Hazard Information | Back Directory | [Chemical Properties]
White powder | [Uses]
Carnosol is a phytopolyphenol found in Rosemary that functions as an antioxidant, antimicrobial, & anticarcinogen. | [Definition]
ChEBI: Carnosol is a diterpenoid. | [Cytotoxicity]
IC50 (μg/mL): 65 (HL-60), 58 (K562), 50(Hep G2), 48 (MCF-7), 53 (MOLT-4)(Farimani et al. 2012)
IC50 (μg/mL): 61.46 (AGS) (Areche et al.2009)
IC50 (μg/mL): 2 (P388) (Aoyagi et al.2006)
IC50 (μg/mL): 1.19 (A2780), 3.30(SW1573), 8.59 (WiDr), 7.93 (T-47D),1.29 (HBL-100) (Guerrero et al. 2006). | [Synthesis]
Take 2000g of dried rosemary branches and leaves, add 14L of petroleum ether, reflux extraction for 3 times, 3 hours each time, merge the 3 extracts, concentrate and recover the petroleum ether, get the extract; dissolve the extract with 40% ethanol, filt | [References]
[1] MARION MAN-YING CHAN Hsing I H Chi Tang Ho. Effects of three dietary phytochemicals from tea, rosemary and turmeric on inflammation-induced nitrite production[J]. Cancer letters, 1995, 96 1: Pages 23-29. DOI: 10.1016/0304-3835(95)03913-h
[2] O I ARUOMA. Antioxidant and pro-oxidant properties of active rosemary constituents: carnosol and carnosic acid.[J]. Xenobiotica, 1992, 22 2: 257-268. DOI: 10.3109/00498259209046624
[3] DANIEL POECKEL . Carnosic acid and carnosol potently inhibit human 5-lipoxygenase and suppress pro-inflammatory responses of stimulated human polymorphonuclear leukocytes[J]. Biochemical pharmacology, 2008, 76 1: Pages 91-97. DOI: 10.1016/j.bcp.2008.04.013
[4] KEITH SINGLETARY Matthew W Christopher MacDonald. Inhibition by rosemary and carnosol of 7,12-dimethylbenz[a]anthracene (DMBA)-induced rat mammary tumorigenesis and in vivo DMBA-DNA adduct formation[J]. Cancer letters, 1996, 104 1: Pages 43-48. DOI: 10.1016/0304-3835(96)04227-9 |
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