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HomeProduct name listCarnosic acid

Carnosic acid

Synonym(s):(4aR,10aS)-5,6-Dihydroxy-7-isopropyl-1,1-dimethyl-1,3,4,9,10,10a-hexahydro-2H-phenanthrene-4a-carboxylic acid;Carnosic acid;Salvin

  • CAS NO.:3650-09-7
  • Empirical Formula: C20H28O4
  • Molecular Weight: 332.43
  • MDL number: MFCD02259459
  • EINECS: 609-253-7
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-06-11 18:14:38
Carnosic acid Structural

What is Carnosic acid?

Description

Carnosic acid (top two images) is a diterpene with an abietane skeleton; rosmarinic acid (bottom two) is a caffeic acid ester.?Both are found in the rosemary plant (Rosmarinus officinalis), each also occurs in other plants.
But carnosic and rosmarinic acids have something else in common:?They are meat preservatives. Rosemary extract was originally added to meat as a flavoring agent, but people noticed that it kept meat from spoiling. It was later discovered that the acids inhibit the free-radical reaction that oxidizes fats and oils and causes spoilage. Neither acid is responsible for the rosemary flavor.

Chemical properties

Yellow powder

The Uses of Carnosic acid

Carnosic 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.

What are the applications of Application

Carnosic acid is an antioxidant, lipid peroxidation inhibitor, and PPARγ activator

Definition

ChEBI: 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.

Anticancer Research

Carnosic acid is a diterpene found in rosemary (Rosmarinus officinalis), exhibitinganti-proliferative effects when observed in vitro in human renal carcinoma cells andcervical carcinoma cells (Su et al. 2016) including inhibition of cell proliferation,angiogenesis and cell migration. ER stress is induced by the carnosic acid present inthe extract from rosemary, inducing cancer cell apoptosis (Cao and Kaufman 2014;Petiwala et al. 2014). Carnosic acid induced dose-dependent expression of ATF4and CHOP and knockdown of CHOP and ATF4 by siRNA-suppressed apoptosis.
The role of ROS was investigated in the induction of ER stress by carnosic acid.ATF4 and CHOP expression induced by carnosic acid was markedly inhibited byROS scavengers. Hence, this information implies that ATF4 and CHOP expressionmediated by ER stress plays a significant part in apoptosis of human kidney Cakicells induced by carnosic acid (Min et al. 2014). Treatment of 22Rv1 and LNCaP,human prostate cancer cell lines, by carnosic acid degraded the androgen receptor(AR), and antigen specific to the prostate also showed reduced expression.Proteasomal degradation pathway dependent on ER stress mediates AR degradation.Induction of CHOP protein, degradation of AR and reduction in the growth ofxenograft prostate cancer tumours by 53% were also detected in vivo. Additionally,carnosic acid induces ER stress only in prostate cancer cells and not in normal cells(Petiwala et al. 2016).

Properties of Carnosic acid

Melting point: 190°C(lit.)
Boiling point: 506.4±50.0 °C(Predicted)
Density  1.184±0.06 g/cm3(Predicted)
storage temp.  Inert atmosphere,Store in freezer, under -20°C
solubility  Chloroform (Slightly), Methanol (Slightly)
form  powder
pka 4.14±0.40(Predicted)
color  yellow
BRN  2707918
CAS DataBase Reference 3650-09-7(CAS DataBase Reference)

Safety information for Carnosic acid

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Carnosic acid

InChIKey QRYRORQUOLYVBU-VBKZILBWSA-N

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