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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 of CARNOSIC ACID

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

Description
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

Sources: Justus Liebigs Annalen der Chemie (1916), 412, 113-36

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
4.3 µM [Ki]
36.0 µM [IC50]
9.2 µM [Ki]
0.24 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Carnosic acid and promotion of monocytic differentiation of HL60-G cells initiated by other agents.
2001 Aug 15
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
Carnosic acid: a potent chemopreventive agent against oral carcinogenesis.
2010 Dec 5
Activation of the nuclear receptor PPARγ by metabolites isolated from sage (Salvia officinalis L.).
2010 Oct 28
Anti-inflammatory effects of supercritical carbon dioxide extract and its isolated carnosic acid from Rosmarinus officinalis leaves.
2011 Apr 27
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
Small molecule activators of the Nrf2-HO-1 antioxidant axis modulate heme metabolism and inflammation in BV2 microglia cells.
2013 Oct
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
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
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
Patents

Sample Use Guides

Rats were treated with Injection of 3 mg/kg Carnosic acid daily for 12 days
Route of Administration: Intraperitoneal
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.
Name Type Language
CARNOSIC ACID
INCI   MI   USP-RS  
INCI  
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)
Created by admin on Fri Dec 15 19:46:52 GMT 2023 , Edited by admin on Fri Dec 15 19:46:52 GMT 2023
Code System Code Type Description
FDA UNII
LI791SXT24
Created by admin on Fri Dec 15 19:46:52 GMT 2023 , Edited by admin on Fri Dec 15 19:46:52 GMT 2023
PRIMARY
RS_ITEM_NUM
1096746
Created by admin on Fri Dec 15 19:46:52 GMT 2023 , Edited by admin on Fri Dec 15 19:46:52 GMT 2023
PRIMARY
MERCK INDEX
m3120
Created by admin on Fri Dec 15 19:46:52 GMT 2023 , Edited by admin on Fri Dec 15 19:46:52 GMT 2023
PRIMARY Merck Index
MESH
C018381
Created by admin on Fri Dec 15 19:46:52 GMT 2023 , Edited by admin on Fri Dec 15 19:46:52 GMT 2023
PRIMARY
WIKIPEDIA
CARNOSIC ACID
Created by admin on Fri Dec 15 19:46:52 GMT 2023 , Edited by admin on Fri Dec 15 19:46:52 GMT 2023
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PUBCHEM
65126
Created by admin on Fri Dec 15 19:46:52 GMT 2023 , Edited by admin on Fri Dec 15 19:46:52 GMT 2023
PRIMARY
CHEBI
65585
Created by admin on Fri Dec 15 19:46:52 GMT 2023 , Edited by admin on Fri Dec 15 19:46:52 GMT 2023
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EPA CompTox
DTXSID20904450
Created by admin on Fri Dec 15 19:46:52 GMT 2023 , Edited by admin on Fri Dec 15 19:46:52 GMT 2023
PRIMARY
CAS
3650-09-7
Created by admin on Fri Dec 15 19:46:52 GMT 2023 , Edited by admin on Fri Dec 15 19:46:52 GMT 2023
PRIMARY