Carnosic Acid
Basic information
- CAS
3650-09-7- Standard SMILES
CC(C)c1cc2c(c(O)c1O)[C@@]1(C(=O)O)CCCC(C)(C)[C@@H]1CC2- InChIKey
QRYRORQUOLYVBU-VBKZILBWSA-N- Molecular formula
- C20H28O4
- Average molar mass
- 332.4 g/mol
- Monoisotopic mass
- 332.19875937
Overview
Carnosic acid is an abietane diterpenoid that is abieta-8,11,13-triene substituted by hydroxy groups at positions 11 and 12 and a carboxy group at position 20. It is isolated from rosemary (Rosmarinus officinalis) and common sage (Salvia officinalis) and exhibits anti-angiogenic, antineoplastic, antioxidant and anti-HIV activity. It has a role as an antioxidant, an antineoplastic agent, a HIV protease inhibitor, an angiogenesis modulating agent, a food preservative, an anti-inflammatory agent, an apoptosis inducer and a plant metabolite. It is a monocarboxylic acid, a member of catechols, an abietane diterpenoid and a carbotricyclic compound. It is a conjugate acid of a carnosate.
Names & identifiers
- Preferred name
- Carnosic Acid
- IUPAC
- (4aR,10aS)-5,6-dihydroxy-1,1-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid
- English name
- Carnosic acid
- Molecular formula
- C20H28O4
- Molecular weight
- 332.43
Names & synonyms
Carnosic acid3650-09-7Salvin11,12-dihydroxyabieta-8,11,13-trien-20-oic acidLI791SXT24CHEBI:65585(4aR,10aS)-5,6-dihydroxy-1,1-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acidRefChem:315844a(2H)-Phenanthrenecarboxylic acid, 1,3,4,9,10,10a-hexahydro-5,6-dihydroxy-1,1-dimethyl-7-(1-methylethyl)-, (4aR,10aS)-609-253-7Rosamox139236-75-2
Show more names
CARNOSOLIC ACID639426carnosicacicarosic acidCamosic acidCARNOSIC ACID(P)CARNOSIC ACID(RG)
RoseOxCarnosic acid (Standard)MFCD02259459Carnosic acid, Free acidNSC694080(4aR,10aS)-5,6-Dihydroxy-7-isopropyl-1,1-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-4a-carboxylic AcidUNII-LI791SXT24Carnosic acid from Rosmarinus officinalis
Database identifiers
Properties
Computed structural properties
- XLogP
- 4.9
- Topological polar surface area
- 77.8 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 500
Physicochemical properties
- Melting point
- 190 °C · 190°C(lit.)
- Boiling point
- 506.4 · 506.4±50.0 °C(Predicted)
- Density
- 1.184 · 1.184±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Inert atmosphere,Store in freezer, under -20°C
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- form
- powder
- pka
- 4.14 · 4.14±0.40(Predicted)
- color
- yellow
- BRN
- 2707918 · 2707918
- Cosmetics Ingredients Functions
- ANTIOXIDANT
- InChI
- 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
- InChIKey
- QRYRORQUOLYVBU-VBKZILBWSA-N
- SMILES
- C1(C)(C)[C@@]2([H])[C@@](C(O)=O)(C3=C(CC2)C=C(C(C)C)C(O)=C3O)CCC1
- LogP
- 5.405 · 5.405 (est)
- CAS DataBase Reference
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory Information4a(2H)-Phenanthrenecarboxylic acid, 1,3,4,9,10,10a-hexahydro-5,6-dihydroxy-1,1-dimethyl-7-(1-methylethyl)-, (4aR,10aS)-: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 29182900
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects.
Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.
Applications
DescriptionCarnosic acid (salvin) is abundant in sage and rosemary leaves. It has antioxidative, anti-carcinogenic, anti-inflammatory, anti-microbial, anti-adipogenic, antiproliferative, antitumorigenic and neuroprotective properties. It is increasingly exploited within food, nutrition health, and cosmetic industries. It is used as the main active antioxidants of food additives in Europe, in products including oils, animal fats, sauces, bakery wares, meat, and fish products etc. to prevent oxidation and prolong their storage time. It is proven to be efficient in the treatment of hyperglycemia. In cosmetic industry, it is used in the hair care and skin care products. Oral health care is another cosmetics-related application of carnosic acid: in vitro studies have shown that it efficiently protected against typical cariogenic microorganisms. It is the important raw material of tooth grinding and gargle agent.
UsesCarnosic Acid is a phenolic component of rosemary. It acts as a potent antioxdant and also has UV protective activity. Specifically protection for UV-A radiation and damage. Carnosic Acid also inhibits the free-radical chain reaction that leads to the oxidation of fats and oils, thereby stabilizing and increasing the shelf life of meats.
Additional notes
DefinitionChEBI: An abietane diterpenoid that is abieta-8,11,13-triene substituted by hydroxy groups at positions 11 and 12 and a carboxy group at position 20. It is isolated from Rosmarinus officinalis and exhibits anti-angiogenic, antineoplastic, antioxidant and anti-HIV activity.
Related reactions
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Compound notes
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