| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:11:32 UTC |
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| Update date | 2019-11-26 03:10:54 UTC |
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| Primary ID | FDB014905 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Carnosic acid |
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| Description | Carnosic acid, also known as carnosate, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Carnosic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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| CAS Number | 3650-09-7 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| Carnosate | Generator | | 11,12-Dihydroxy-8,11,13-abietatrien-20-oic acid | db_source | | 2,4(1H,3H)-Pyrimidinedione, 5-fluorodihydro-6-hydroxy- | biospider | | 4a(2H)-Phenanthrenecarboxylic acid | HMDB | | Carnosic acid | db_source | | Deoxypicrosalvinic acid | db_source | | RoseOx | HMDB | | Salvin | HMDB | | Salvin? | db_source |
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| Predicted Properties | |
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| Chemical Formula | C20H28O4 |
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| IUPAC name | 5,6-dihydroxy-1,1-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-4a-carboxylic acid |
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| InChI Identifier | 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) |
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| InChI Key | QRYRORQUOLYVBU-UHFFFAOYSA-N |
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| Isomeric SMILES | CC(C)C1=CC2=C(C(O)=C1O)C1(CCCC(C)(C)C1CC2)C(O)=O |
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| Average Molecular Weight | 332.4339 |
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| Monoisotopic Molecular Weight | 332.198759384 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Prenol lipids |
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| Sub Class | Diterpenoids |
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| Direct Parent | Diterpenoids |
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| Alternative Parents | |
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| Substituents | - Abietane diterpenoid
- Diterpenoid
- Hydrophenanthrene
- Phenanthrene
- 1-naphthalenecarboxylic acid
- 1-naphthalenecarboxylic acid or derivatives
- Tetralin
- 1-hydroxy-4-unsubstituted benzenoid
- Benzenoid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Organic oxide
- Organic oxygen compound
- Aromatic homopolycyclic compound
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| Molecular Framework | Aromatic homopolycyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Ontology | No ontology term |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
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| Physical state | Solid | |
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| Physical Description | Not Available | |
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| Mass Composition | C 72.26%; H 8.49%; O 19.25% | DFC |
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| Melting Point | Mp 185-190° dec. | DFC |
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| Boiling Point | Not Available | |
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| Experimental Water Solubility | Not Available | |
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| Experimental logP | Not Available | |
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| Experimental pKa | Not Available | |
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| Isoelectric point | Not Available | |
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| Charge | Not Available | |
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| Optical Rotation | [a]23D +191 (c, 1.07 in MeOH) | DFC |
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| Spectroscopic UV Data | 284 (e 1690) (EtOH) (Berdy) | DFC |
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| Density | Not Available | |
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| Refractive Index | Not Available | |
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| Spectra |
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| Spectra | Not Available |
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| External Links |
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| ChemSpider ID | 400886 |
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| ChEMBL ID | Not Available |
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| KEGG Compound ID | Not Available |
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| Pubchem Compound ID | 455260 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | Not Available |
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| Phenol-Explorer ID | 666 |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB02358 |
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| CRC / DFC (Dictionary of Food Compounds) ID | KWD08-Y:JXH93-K |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | SALVIN|CARNOSIC-ACID |
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| BIGG ID | Not Available |
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| KNApSAcK ID | Not Available |
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| HET ID | Not Available |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Not Available |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | | Descriptor | ID | Definition | Reference |
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| Anti bacterial | 33282 | An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis. | DUKE | | Anti-mutagenic | | An agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects. | DUKE | | Anti-oxidant | 22586 | An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects. | DUKE | | Anti septic | 33281 | An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management. | DUKE | | Pesticide | 25944 | An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections. | DUKE |
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| Enzymes | Not Available |
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| Pathways | Not Available |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | Not Available |
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| Files |
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| MSDS | show |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| Content Reference | — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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