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Key Documents

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.

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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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
Seitaro Nakagawa et al.
Antibiotics (Basel, Switzerland), 9(4) (2020-04-05)
Staphylococcus aureus is an opportunistic pathogen and a common cause of skin infection. S. aureus also plays a role in the pathogenesis of the chronic inflammatory skin disease, atopic dermatitis. S. aureus virulence involves activation of the quorum sensing agr
Kyung-Soo Chun et al.
Journal of cancer prevention, 19(2), 103-110 (2014-10-23)
Cancer is an unbeaten health challenge for the humankind. After striving for decades to find a cancer cure, attention has now been shifted to reduce the morbidity and mortality from cancer by halting the course of tumor development. Numerous bioactive
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
Auxiliadora López-Jiménez et al.
European journal of nutrition, 52(1), 85-95 (2011-12-17)
The use of rosemary (Rosmarinus officinalis) leaves and their constituents as a source of dietary antioxidants and flavoring agents is continuously growing. Carnosol and carnosic acid, two major components of rosemary extracts, have shown activity for cancer prevention and therapy.

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