ChemicalBook CAS DataBase List 3650-09-7

3650-09-7

Name	Carnosic acid
CAS	3650-09-7
EINECS(EC#)	609-253-7
Molecular Formula	C20H28O4
MDL Number	MFCD02259459
Molecular Weight	332.43
MOL File	3650-09-7.mol

Chemical Properties

Melting point	190°C(lit.)
Boiling point	506.4±50.0 °C(Predicted)
density	1.184±0.06 g/cm3(Predicted)
storage temp.	−20°C
solubility	Chloroform (Slightly), Methanol (Slightly)
form	powder
pka	4.14±0.40(Predicted)
color	yellow
BRN	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 (est)
CAS DataBase Reference	3650-09-7(CAS DataBase Reference)

Safety Data

Symbol(GHS)	GHS07
Signal word	Warning
Hazard statements	H302-H315-H319-H335
Precautionary statements	P261-P305+P351+P338
Safety Statements	S22:Do not breathe dust . S24/25:Avoid contact with skin and eyes . less more
WGK Germany	3
HS Code	29182900
Storage Class	11 - Combustible Solids

Hazard Information

Chemical Properties

Yellow powder

Uses

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.

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).

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3650-09-7

Chemical Properties

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Chemical Properties

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Definition

Anticancer Research

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