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
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
| 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 |
DescriptionCurator'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
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 | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL340 |
4.3 µM [Ki] | ||
Target ID: CHEMBL1812 |
36.0 µM [IC50] | ||
Target ID: CHEMBL3397 |
9.2 µM [Ki] | ||
Target ID: CHEMBL2366517 |
0.24 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
|
| Novel screening method for potential skin-whitening compounds by a luciferase reporter assay. | 2010 |
|
| 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 |
|
| Sirtuin 1-mediated inhibition of p66shc expression alleviates liver ischemia/reperfusion injury. | 2014 May |
|
| 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.
| Substance Class |
Chemical
Created
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admin
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Edited
Fri Dec 15 19:46:52 GMT 2023
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| Record UNII |
LI791SXT24
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| Record Status |
Validated (UNII)
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672 (Number of products:2)
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m3120
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C018381
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CARNOSIC ACID
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PARENT -> CONSTITUENT ALWAYS PRESENT |
