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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.

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

signalword

Warning

hcodes

H317

Hazard Classifications

Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

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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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)
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
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
N Mulinacci et al.
Talanta, 85(1), 167-176 (2011-06-08)
The Rosmarinus officinalis L. is widely known for its numerous applications in the food field but also for the increasing interest in its pharmaceutical properties. Two groups of compounds are mainly responsible for the biological activities of the plant: the
Yosei Tamaki et al.
Planta medica, 76(7), 683-688 (2009-11-27)
In our previous studies, we have reported that carnosic acid (CA) and carnosol (CS) originating from rosemary protects cortical neurons by inducing phase 2 enzymes, the induction of which was initiated by activation of the Keap1/Nrf2 pathway , , .
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