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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:
Molecular Weight:
330.42
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.25

biological source

Rosemarinus officinalis L.

Quality Level

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

Signal Word

Warning

Hazard Statements

Precautionary Statements

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)

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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
Marvin J Núñez et al.
Phytochemistry, 72(4-5), 385-390 (2011-02-15)
Two ent-rosane- (cuzcol, 1 and 6-dehydroxycuzcol, 2) and a abietatriene- (salvadoriol, 3) type diterpenoids have been isolated from Maytenus cuzcoina and Crossopetalum uragoga, respectively, along with five known diterpene compounds (4-8). Their stereostructures have been elucidated on the basis of

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