A phenol with diverse biological activities
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Carnosol

Item No. 89800

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1,3,4,9,10,10aS-hexahydro-5,6-dihydroxy-1,1-dimethyl-7-isopropyl-2H-9S,4aR-(epoxymethano)phenanthren-12-one
CAS Number
5957-80-2
Synonyms
  • NSC 39143
Molecular Formula
C20H26O4
Formula Weight
330.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: >35 mg/mlDMSO: >250 mg/mlEthanol: >8 mg/mlEthanol:PBS(pH 7.2)(1:1): 0.5 mg/mlPBS pH 7.2: <30 µg/ml
λmax
285 nm
SMILES
CC(C)c1cc2C3OC(=O)C4(CCCC(C)(C)C4C3)c2c(O)c1O
InChi Code
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?/m1/s1
InChi Key
XUSYGBPHQBWGAD-LQZXRHCMSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

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    Cayman Chemical
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    Product Description

    Carnosol is a phenol that has been found in rosemary (R. officinalis) and has diverse biological activities.1,2,3,4 It decreases nitric oxide (NO) production in mouse peritoneal exudate macrophages when used at concentrations ranging from 6 to 25 µM.1 Carnosol scavenges peroxyl and hydroxyl radicals and inhibits lipid peroxidation in cell-free assays.2 It inhibits 5-lipoxygenase (5-LO; IC50 = 0.1 µM for the recombinant human enzyme) and the synthesis of leukotrienes in human polymorphonuclear leukocytes (PMNs; IC50 = 7 µM).3 In vivo, carnosol (200 mg/kg) reduces mammary DNA adduct formation and tumorigenesis in a rat model of DMBA-induced mammary tumorigenesis.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chan, M.M., Ho, C.T., and Huang, H.I. Effects of three dietary phytochemicals from tea, rosemary, and turmeric on inflammation-induced nitrite production. Cancer Lett. 96(1), 23-29 (1995).

    2. Aruoma, O.I., Halliwell, B., Aeschbach, R., et al. Antioxidant and pro-oxidant properties of active rosemary constituents: Carnosol and carnosic acid. Xenobiotica 22(2), 257-268 (1992).

    3. Poeckel, D., Greiner, C., Verhoff, M., et al. Carnosic acid and carnosol potently inhibit human 5-lipoxygenase and suppress pro-inflammatory responses of stimulated human polymorphonuclear leukocytes. Biochem. Pharmacol. 76(1), 91-97 (2008).

    4. Singletary, K., MacDonald, C., and Wallig, M. Inhibition by rosemary and carnosol of 7,12-dimethylbenz[a]anthracene (DMBA)-induced rat mammary tumorigenesis and in vivo DMBA-DNA adduct formation. Cancer Lett. 104(1), 43-48 (1996).