CARNOSIC ACID

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H28O4
Molecular Weight	332.4339
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CCC3=C(C(O)=C(O)C(=C3)C(C)C)[C@]1(CCCC2(C)C)C(O)=O

InChI

InChIKey=QRYRORQUOLYVBU-VBKZILBWSA-N

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

HIDE SMILES / InChI

Molecular Formula	C20H28O4
Molecular Weight	332.4339
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25639596
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/28918123 | https://www.ncbi.nlm.nih.gov/pubmed/28916593 | https://www.ncbi.nlm.nih.gov/pubmed/28887507 | https://www.ncbi.nlm.nih.gov/pubmed/18848780 | https://www.ncbi.nlm.nih.gov/pubmed/22531045

Carnosic acid [CA, (4aR,10aS)-5,6-dihydroxy-1,1-dimethyl-7- propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid] is a phenolic diterpene found in the leaves of the rosemary plant (Rosmarinus officinalis) and is used routinely as a food and cosmetic additive due to its antioxidant and antimicrobial properties. Carnosic acid as a food additive has a good safety profile and does not pose a health concern. Carnosic acid has demonstrated anti-inflammatory, anticancer, photoprotective, and antiadipogenic activities in vitro. Carnosic acid was shown to induce significant weight loss and reduced visceral adiposity in ob/ob mice fed a diet supplemented with carnosic acid. Carnosic acid is used as a preservative or antioxidant in food and nonfood products (e.g. toothpaste, mouthwash and chewing gum) -in which it has an antimicrobial effect on the microbes responsible for bad breath- or in skin care products.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cytochrome P450 3A4 127 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22531045	Substrate 661	4.3 µM [Ki]
Pancreatic lipase 5 Target ID: CHEMBL1812 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17521912	Inhibitor 8297	36.0 µM [IC50]
Cytochrome P450 2C9 50 Target ID: CHEMBL3397 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22531045	Substrate 661	9.2 µM [Ki]
Protease 7 Target ID: CHEMBL2366517 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19813754	Inhibitor 8297	0.24 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Ultraviolet-induced erythema 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17713873	Primary		Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Carnosic acid and promotion of monocytic differentiation of HL60-G cells initiated by other agents.	2001 Aug 15	11504768
Carnosic acid protects neuronal HT22 Cells through activation of the antioxidant-responsive element in free carboxylic acid- and catechol hydroxyl moieties-dependent manners.	2008 Apr 4	18329808
Novel screening method for potential skin-whitening compounds by a luciferase reporter assay.	2010	21071833
Carnosic acid: a potent chemopreventive agent against oral carcinogenesis.	2010 Dec 5	20816777
Activation of the nuclear receptor PPARγ by metabolites isolated from sage (Salvia officinalis L.).	2010 Oct 28	20696231
Anti-inflammatory effects of supercritical carbon dioxide extract and its isolated carnosic acid from Rosmarinus officinalis leaves.	2011 Apr 27	21375325
Synergism between carnosic acid and arsenic trioxide on induction of acute myeloid leukemia cell apoptosis is associated with modulation of PTEN/Akt signaling pathway.	2012 Dec	23239002
Small molecule activators of the Nrf2-HO-1 antioxidant axis modulate heme metabolism and inflammation in BV2 microglia cells.	2013 Oct	23942037
Sirtuin 1-mediated inhibition of p66shc expression alleviates liver ischemia/reperfusion injury.	2014 May	24557422
Induction of Pi form of glutathione S-transferase by carnosic acid is mediated through PI3K/Akt/NF-κB pathway and protects against neurotoxicity.	2014 Nov 17	25271104
Role for the PI3K/Akt/Nrf2 signaling pathway in the protective effects of carnosic acid against methylglyoxal-induced neurotoxicity in SH-SY5Y neuroblastoma cells.	2015 Dec 5	26577515
Carnosic acid protects against 6-hydroxydopamine-induced neurotoxicity in in vivo and in vitro model of Parkinson's disease: involvement of antioxidative enzymes induction.	2015 Jan 5	25446857

Patents

Sample Use Guides

In Vivo Use Guide

Rats were treated with Injection of 3 mg/kg Carnosic acid daily for 12 days

Route of Administration: Intraperitoneal

In Vitro Use Guide

The MIC of Carnosic acid was determined against S. aureus 1199 and S. aureus 1199B in Muller–Hinton Broth in the presence of increasing amounts of efflux pump inhibitors by broth checkerboard synergy method in a microtitre plates using twofold serial dilutions. Each candidate EPI was tested at seven concentrations (100–1.56 mkg/mL). The plates were incubated for 18 h at 37 C and the wells were assessed visually for growth. The minimal effective concentration (MEC) was determined to be the minimal concentration of EPI that produced the maximal reduction in substrate MIC.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:46:52 UTC 2023` Edited by `admin` on `Fri Dec 15 19:46:52 UTC 2023`
Record UNII	LI791SXT24
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CARNOSIC ACID

Official Name

English

(4AR,10AS)-1,3,4,9,10,10A-HEXAHYDRO-5,6-DIHYDROXY-1,1-DIMETHYL-7-(1-METHYLETHYL)-4A(2H)-PHENANTHRENECARBOXYLIC ACID

Common Name

English

CARNOSIC ACID [USP-RS]

Common Name

English

SALVIN

Common Name

English

CARNOSIC ACID (CONSTITUENT OF ROSEMARY) [DSC]

Common Name

English

CARNOSIC ACID [INCI]

Common Name

English

CARNOSIC ACID [MI]

Common Name

English

Classification Tree Code System Code

DSLD

672 (Number of products:2)