Carnosic Acid | Salvin | CAS#3650-09-7

MedKoo Cat#: 600120 | Name: Carnosic Acid

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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 has medicinal properties, is a potent antioxidant and protects skin cells against UV-A radiation (photoprotection). Studies in animals have also found a protection against carcinogens. 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).

Chemical Structure

Carnosic Acid

CAS#3650-09-7

Theoretical Analysis

MedKoo Cat#: 600120

Name: Carnosic Acid

CAS#: 3650-09-7

Chemical Formula: C20H28O4

Exact Mass: 332.1988

Molecular Weight: 332.43

Elemental Analysis: C, 72.26; H, 8.49; O, 19.25

Price and Availability

Size	Price	Availability
1g	USD 250.00	2 Weeks
2g	USD 350.00	2 Weeks
5g	USD 550.00	2 Weeks
10g	USD 850.00	2 Weeks

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Related CAS #

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Synonym

Salvin; Carnosic Acid;

IUPAC/Chemical Name

(4aR,10aS)-5,6-dihydroxy-1,1-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid

InChi Key

QRYRORQUOLYVBU-VBKZILBWSA-N

InChi Code

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

SMILES Code

O=C([C@]12CCCC(C)(C)[C@]1([H])CCC3=C2C(O)=C(O)C(C(C)C)=C3)O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO.

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Carnosic acid (Salvin) is a phenolic diterpene, endowed with antioxidative and antimicrobial properties.

In vitro activity:

The objective of this study was to examine whether carnosic acid (CA), the main antioxidant compound of Rosmarinus officinalis L., would inhibit the cell viability of three CRC cell lines: Caco-2, HT29 and LoVo in a dose-dependent manner, with IC₅₀ values in the range of 24-96 µM. CA induced cell death by apoptosis in Caco-2 line after 24 h of treatment and inhibited cell adhesion and migration, possibly by reducing the activity of secreted proteases such as urokinase plasminogen activator (uPA) and metalloproteinases (MMPs). These effects may be associated through a mechanism involving the inhibition of the COX-2 pathway, because we have determined that CA downregulates the expression of COX-2 in Caco-2 cells at both the mRNA and protein levels. Therefore, CA modulates different targets involved in the development of CRC. These findings indicate that carnosic acid may have anticancer activity and may be useful as a novel chemotherapeutic agent. Reference: Oncol Rep. 2012 Apr;27(4):1041-8. doi: 10.3892/or.2012.1630. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/22246562/

In vivo activity:

Carnosic acid (CA) was used to treat collagen-induced arthritis (CIA)-induced db/db mice. Blood glucose, oral glucose tolerance test (OGTT) and insulin tolerance test (ITT) were investigated to explore insulin resistance. CA significantly down-regulated fasting blood glucose, glucose level in OGTT and ITT, ameliorated CIA-induced bone loss, and reduced pro-inflammatory cytokines and reactive oxygen species (ROS) in db/db mice with arthritis induced by CIA. Reference: Free Radic Biol Med. 2017 Jul;108:418-432. https://linkinghub.elsevier.com/retrieve/pii/S0891-5849(17)30172-7

	Solvent	mg/mL	mM
Solubility
	DMSO	66.0	198.54

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 332.43 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

In vitro protocol:

1. Barni MV, Carlini MJ, Cafferata EG, Puricelli L, Moreno S. Carnosic acid inhibits the proliferation and migration capacity of human colorectal cancer cells. Oncol Rep. 2012 Apr;27(4):1041-8. doi: 10.3892/or.2012.1630. Epub 2012 Jan 11. PMID: 22246562; PMCID: PMC3583532. 2. de Oliveira MR. Carnosic Acid as a Promising Agent in Protecting Mitochondria of Brain Cells. Mol Neurobiol. 2018 Aug;55(8):6687-6699. doi: 10.1007/s12035-017-0842-6. Epub 2018 Jan 15. PMID: 29335845.

In vivo protocol:

1. Xia G, Wang X, Sun H, Qin Y, Fu M. Carnosic acid (CA) attenuates collagen-induced arthritis in db/db mice via inflammation suppression by regulating ROS-dependent p38 pathway. Free Radic Biol Med. 2017 Jul;108:418-432. doi: 10.1016/j.freeradbiomed.2017.03.023. Epub 2017 Mar 23. PMID: 28343998.

1: Satoh T, Trudler D, Oh CK, Lipton SA. Potential Therapeutic Use of the Rosemary Diterpene Carnosic Acid for Alzheimer's Disease, Parkinson's Disease, and Long-COVID through NRF2 Activation to Counteract the NLRP3 Inflammasome. Antioxidants (Basel). 2022 Jan 6;11(1):124. doi: 10.3390/antiox11010124. PMID: 35052628; PMCID: PMC8772720. 2: Cheng J, Xu T, Xun C, Guo H, Cao R, Gao S, Sheng W. Carnosic acid protects against ferroptosis in PC12 cells exposed to erastin through activation of Nrf2 pathway. Life Sci. 2021 Feb 1;266:118905. doi: 10.1016/j.lfs.2020.118905. Epub 2020 Dec 14. PMID: 33333051. 3: Birtić S, Dussort P, Pierre FX, Bily AC, Roller M. Carnosic acid. Phytochemistry. 2015 Jul;115:9-19. doi: 10.1016/j.phytochem.2014.12.026. Epub 2015 Jan 29. PMID: 25639596. 4: Mirza FJ, Zahid S, Holsinger RMD. Neuroprotective Effects of Carnosic Acid: Insight into Its Mechanisms of Action. Molecules. 2023 Mar 2;28(5):2306. doi: 10.3390/molecules28052306. PMID: 36903551; PMCID: PMC10005014. 5: de Oliveira MR. Carnosic Acid as a Promising Agent in Protecting Mitochondria of Brain Cells. Mol Neurobiol. 2018 Aug;55(8):6687-6699. doi: 10.1007/s12035-017-0842-6. Epub 2018 Jan 15. PMID: 29335845. 6: Farhadi F, Baradaran Rahimi V, Mohamadi N, Askari VR. Effects of rosmarinic acid, carnosic acid, rosmanol, carnosol, and ursolic acid on the pathogenesis of respiratory diseases. Biofactors. 2023 May-Jun;49(3):478-501. doi: 10.1002/biof.1929. Epub 2022 Dec 23. PMID: 36564953. 7: Bahri S, Jameleddine S, Shlyonsky V. Relevance of carnosic acid to the treatment of several health disorders: Molecular targets and mechanisms. Biomed Pharmacother. 2016 Dec;84:569-582. doi: 10.1016/j.biopha.2016.09.067. Epub 2016 Sep 29. PMID: 27694001. 8: Moore J, Yousef M, Tsiani E. Anticancer Effects of Rosemary (Rosmarinus officinalis L.) Extract and Rosemary Extract Polyphenols. Nutrients. 2016 Nov 17;8(11):731. doi: 10.3390/nu8110731. PMID: 27869665; PMCID: PMC5133115. 9: El-Huneidi W, Bajbouj K, Muhammad JS, Vinod A, Shafarin J, Khoder G, Saleh MA, Taneera J, Abu-Gharbieh E. Carnosic Acid Induces Apoptosis and Inhibits Akt/mTOR Signaling in Human Gastric Cancer Cell Lines. Pharmaceuticals (Basel). 2021 Mar 8;14(3):230. doi: 10.3390/ph14030230. PMID: 33800129; PMCID: PMC7998299. 10: Ghasemzadeh Rahbardar M, Hemadeh B, Razavi BM, Eisvand F, Hosseinzadeh H. Effect of carnosic acid on acrylamide induced neurotoxicity: in vivo and in vitro experiments. Drug Chem Toxicol. 2022 Jul;45(4):1528-1535. doi: 10.1080/01480545.2020.1845715. Epub 2020 Nov 19. PMID: 33213219. 11: Kim JY, Hong HL, Kim GM, Leem J, Kwon HH. Protective Effects of Carnosic Acid on Lipopolysaccharide-Induced Acute Kidney Injury in Mice. Molecules. 2021 Dec 14;26(24):7589. doi: 10.3390/molecules26247589. PMID: 34946671; PMCID: PMC8705858. 12: Razavi BM, Abazari AR, Rameshrad M, Hosseinzadeh H. Carnosic acid prevented olanzapine-induced metabolic disorders through AMPK activation. Mol Biol Rep. 2020 Oct;47(10):7583-7592. doi: 10.1007/s11033-020-05825-5. Epub 2020 Sep 14. PMID: 32929650. 13: McCord JM, Hybertson BM, Cota-Gomez A, Gao B. Nrf2 activator PB125® as a carnosic acid-based therapeutic agent against respiratory viral diseases, including COVID-19. Free Radic Biol Med. 2021 Nov 1;175:56-64. doi: 10.1016/j.freeradbiomed.2021.05.033. Epub 2021 May 28. PMID: 34058321; PMCID: PMC8413148. 14: de Oliveira MR. The Dietary Components Carnosic Acid and Carnosol as Neuroprotective Agents: a Mechanistic View. Mol Neurobiol. 2016 Nov;53(9):6155-6168. doi: 10.1007/s12035-015-9519-1. Epub 2015 Nov 9. PMID: 26553346. 15: Dessai A, Shetty N, Saralaya V, Natarajan S, Mala K. Carnosic Acid as an intracanal medicament performs better than triple antibiotic paste and calcium hydroxide to eradicate Enterococcus faecalis from root canal: An in vitro confocal laser scanning microscopic study. J Conserv Dent. 2022 Jan- Feb;25(1):20-25. doi: 10.4103/jcd.jcd_317_21. Epub 2022 May 2. PMID: 35722077; PMCID: PMC9200188. 16: Den Hartogh DJ, Vlavcheski F, Giacca A, MacPherson REK, Tsiani E. Carnosic Acid Attenuates the Free Fatty Acid-Induced Insulin Resistance in Muscle Cells and Adipocytes. Cells. 2022 Jan 5;11(1):167. doi: 10.3390/cells11010167. PMID: 35011728; PMCID: PMC8750606. 17: Lee DK, Jang HD. Carnosic Acid Attenuates an Early Increase in ROS Levels during Adipocyte Differentiation by Suppressing Translation of Nox4 and Inducing Translation of Antioxidant Enzymes. Int J Mol Sci. 2021 Jun 5;22(11):6096. doi: 10.3390/ijms22116096. PMID: 34198827; PMCID: PMC8201016. 18: Hosokawa I, Hosokawa Y, Ozaki K, Matsuo T. Carnosic Acid Inhibits CXCR3 Ligands Production in IL-27-Stimulated Human Oral Epithelial Cells. Inflammation. 2019 Aug;42(4):1311-1316. doi: 10.1007/s10753-019-00991-6. PMID: 30820808. 19: Azhar M, Zeng G, Ahmed A, Dar Farooq A, Choudhary MI, De-Jiang J, Liu X. Carnosic acid ameliorates depressive-like symptoms along with the modulation of FGF9 in the hippocampus of middle carotid artery occlusion-induced Sprague Dawley rats. Phytother Res. 2021 Jan;35(1):384-391. doi: 10.1002/ptr.6810. Epub 2020 Aug 11. PMID: 32779789. 20: Han L, Li L, Wu G. Induction of ferroptosis by carnosic acid-mediated inactivation of Nrf2/HO-1 potentiates cisplatin responsiveness in OSCC cells. Mol Cell Probes. 2022 Aug;64:101821. doi: 10.1016/j.mcp.2022.101821. Epub 2022 Apr 29. PMID: 35490795.