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: 2024-11-19 23:02:33
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) |
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 |
Carnosic acid manufacturer
Phytotech Extract Pvt Ltd
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