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Carnosic acid

Carnosic acid structure

Carnosic acid 

structure
  • CAS No:

    3650-09-7

  • Formula:

    C20H28O4

  • Chemical Name:

    Carnosic acid

  • Synonyms:

    4a(2H)-Phenanthrenecarboxylic acid,1,3,4,9,10,10a-hexahydro-5,6-dihydroxy-1,1-dimethyl-7-(1-methylethyl)-,(4aR,10aS)-;Podocarpa-8,11,13-trien-17-oic acid,11,12-dihydroxy-13-isopropyl-;4a(2H)-Phenanthrenecarboxylic acid,1,3,4,9,10,10a-hexahydro-5,6-dihydroxy-1,1-dimethyl-7-(1-methylethyl)-,(4aR-trans)-;(4aR,10aS)-1,3,4,9,10,10a-Hexahydro-5,6-dihydroxy-1,1-dimethyl-7-(1-methylethyl)-4a(2H)-phenanthrenecarboxylic acid;Carnosic acid;Salvin;RoseOx;Rosamox;(+)-Carnosic acid;(4AR,10aS)-5,6-dihydroxy-1,1-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid

  • Categories:

    Cosmetic Ingredient  >  Antioxidant Ingredient

Description

Carnosic acid has demonstrated inhibition of oxidative stress and inflammation, suppression of cell proliferation, and antibacterial activity.


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 antineoplastic agent, an antioxidant, a HIV protease inhibitor, an angiogenesis modulating agent, an apoptosis inducer, a plant metabolite, an anti-inflammatory agent and a food preservative. It is an abietane diterpenoid, a carbotricyclic compound, a member of catechols and a monocarboxylic acid. It is a conjugate acid of a carnosate.

Carnosic acid Basic Attributes

332.43400

332.43

609-253-7

LI791SXT24

694080

29182900

Characteristics

77.76000

4.9

yellow powder

1.184 g/cm3

201-202 °C

506.4ºC at 760 mmHg

274.2ºC

1.575

-20ºC

Safety Information

NONH for all modes of transport

3

S22; S24/25

Drug Information

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. (See all compounds classified as Anti-Infective Agents, Local.)|Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)

carnosic acid

Carnosic acid Use and Manufacturing

Carnosic acid is a natural benzenediol abietane diterpene found in rosemary (Rosmarinus officinalis) and common sage (Salvia officinalis). Dried leaves of rosemary or sage contain 1.5 to 2.5% 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 skin care products).

Computed Properties

Molecular Weight:332.4
XLogP3:4.9
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:332.19875937
Monoisotopic Mass:332.19875937
Topological Polar Surface Area:77.8
Heavy Atom Count:24
Complexity:500
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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