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C9617

Sigma-Aldrich

Carnosol

Synonym(s):

Picrosalvin

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About This Item

Empirical Formula (Hill Notation):
C20H26O4
CAS Number:
5957-80-2
Molecular Weight:
330.42
MDL number:
MFCD02752467
UNSPSC Code:
12352100
PubChem Substance ID:
329775081
NACRES:
NA.25

biological source

Rosemarinus officinalis L.

Quality Level

200

form

powder

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

shipped in

dry ice

storage temp.

−20°C

SMILES string

CC(C)c1cc2[C@@H]3C[C@H]4C(C)(C)CCC[C@]4(C(=O)O3)c2c(O)c1O

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

InChI key

XUSYGBPHQBWGAD-PJSUUKDQSA-N

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General description

Carnosol (CAR) is an ortho-diphenolic diterpene, extracted from the Mediterranean dietary herb Rosmarinus officinalis L. (rosemary). It was first isolated from the Salvia carnosa (Sage) plant. Carnosol is also a pro-electrophilic molecule.

Application

Carnosol has been used as an anti-cancer agent:
  • to test its anti-cancer and anti-proliferative activities on cancer stem-like cells (CSCs) and Glioblastoma multiforme (GBM) cells
  • to inspect its anti-carcinogenic effects on nineteen genes involved in up-and down-regulation of different genetic carcinogenesis pathways and on HeLa cells in human cervical cancer model
  • as a reference standard to identify and quantify the metabolites of rosemary extract using liquid chromatography coupled to tandem mass spectrometry (LC/ESI-MS/MS)

Biochem/physiol Actions

Carnosol together with carnosic acid (CA) accounts for 90% of the antioxidant activity of rosemary leaves. It exerts neuroprotective properties and protects against neuroinflammation, and oxidative stress-induced brain damage under chronic stress conditions. Carnosol is a strong chemo-therapeutic agent studied for several types of cancer like breast, leukemia, skin, prostate, and colon. It is also an antimicrobial agent.
A phenolic diterpene with antioxidant and anticarcinogenic activities.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317

Precautionary Statements

P280 - P302 + P352

Hazard Classifications

Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Marcos Roberto de Oliveira
Molecular neurobiology, 53(9), 6155-6168 (2016-11-01)
Carnosic acid (CA) and carnosol are the major diterpenes found in Rosmarinus officinalis (rosemary), a culinary spice. CA and carnosol account for over 90 % of its anti-oxidant activity in rosemary leaves. The diterpenes exert anti-oxidant, anti-inflammatory, and anti-carcinogenic activities, and
The anticancer molecular mechanism of Carnosol in human cervical cancer cells: An in vitro study
Hafidha RR and Abdulamirb AS
Asia-Pacific Journal of Molecular Biology and Biotechnology, 88-98 (2020)
Lucia Cattaneo et al.
PloS one, 10(7), e0132439-e0132439 (2015-07-16)
Rosemary (Rosmarinus officinalis L.) has been used since ancient times in traditional medicine, while nowadays various rosemary formulations are increasingly exploited by alternative medicine to cure or prevent a wide range of health disorders. Rosemary's bioproperties have prompted scientific investigation
Saeed Samarghandian et al.
BMC complementary and alternative medicine, 17(1), 249-249 (2017-05-06)
Oxidative stress through chronic stress destroys the brain function. There are many documents have shown that carnosol may have a therapeutic effect versus free radical induced diseases. The current research focused the protective effect of carnosol against the brain injury
Andreja Sinkovic et al.
Phytotherapy research : PTR, 25(3), 402-407 (2010-08-25)
Polyphenol antioxidants decrease the risk of atherosclerosis. The study aimed to evaluate prospectively in healthy young participants the effect of oral rosemary extracts (RE), consisting of diphenols, upon endothelial dysfunction (ED), preceding structural atherosclerosis. Nineteen healthy young volunteers were studied
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