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C0609

Sigma-Aldrich

Carnosic acid from Rosmarinus officinalis

≥91%, powder

Synonym(s):

(4AR,10aS)-5,6-dihydroxy-1,1-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C20H28O4
CAS Number:
3650-09-7
Molecular Weight:
332.43
MDL number:
MFCD02259459
UNSPSC Code:
12352106
PubChem Substance ID:
329774804
NACRES:
NA.25

Quality Level

200

assay

≥91%

form

powder

color

faintly yellow to dark yellow

shipped in

wet ice

storage temp.

−20°C

SMILES string

CC(C)c1cc2CC[C@H]3C(C)(C)CCC[C@]3(C(O)=O)c2c(O)c1O

InChI

1S/C20H28O4/c1-11(2)13-10-12-6-7-14-19(3,4)8-5-9-20(14,18(23)24)15(12)17(22)16(13)21/h10-11,14,21-22H,5-9H2,1-4H3,(H,23,24)/t14-,20+/m0/s1

InChI key

QRYRORQUOLYVBU-VBKZILBWSA-N

Application

Carnosic acid from Rosmarinus officinalis is used to study its mechanisms as an antioxidant that protects lipids from peroxidation and proteins from carbonylation. Carnosic acid is used to assess its neuroprotective activies including its ability to modulate the neurotoxic effects of 6-hydroxydopamine (6-OHDA). Carnosic acid may also be used to study it anticancer potential.
Phenolic compound that is naturally occurring with antioxidant properties. Inhibits lipid peroxidation which is caused by NADH or NADPH oxidation.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tayebeh Rezaie et al.
Investigative ophthalmology & visual science, 53(12), 7847-7854 (2012-10-20)
The herb rosemary has been reported to have antioxidant and anti-inflammatory activity. We have previously shown that carnosic acid (CA), present in rosemary extract, crosses the blood-brain barrier to exert neuroprotective effects by upregulating endogenous antioxidant enzymes via the Nrf2
A I Kuzmenko et al.
Journal of photochemistry and photobiology. B, Biology, 48(1), 63-67 (1999-04-17)
Lipid free-radical oxidation has been studied in vivo in the mitochondrial fractions of the liver of rats fed RoseOx (carnosic acid nutritional supplement) by measuring chemiluminescence. The kinetics of the lipid chemiluminescence in rats fed RoseOx are significantly different from
Mariano Walter Pertino et al.
Journal of natural products, 73(4), 639-643 (2010-04-03)
Carnosic acid (1) has been shown to possess gastroprotective activity in vitro and in vivo. However, little is known of the gastroprotective effect or cytotoxicity of carnosic acid gamma-lactone (3). To determine structure-activity relationships, a series of 17 esters of
Riham Salah El Dine et al.
Journal of natural products, 72(11), 2019-2023 (2009-10-10)
A new farnesyl hydroquinone, ganomycin I (1), was isolated along with ganomycin B (2) from the chloroform extract of the fruiting bodies of the Vietnamese mushroom Ganoderma colossum. These compounds inhibited HIV-1 protease with IC50 values of 7.5 and 1.0
Carnosic acid attenuates lipopolysaccharide-induced liver injury in rats via fortifying cellular antioxidant defense system.
Xiang Q, Liu Z, Wang Y, Xiao H, et al.
Food And Chemical Toxicology (2012)
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