Calendic Acid | CAS#5204-87-5

MedKoo Cat#: 462943 | Name: Calendic Acid

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Description:

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

Calendic Acid is a conjugated polyunsaturated fatty acid that has been found in C. officinalis seed oil and has anticancer activity. It inhibits the growth of Caco-2 cells when used at concentrations ranging from 10 to 50 µM. Calendic Acid induces formation of thiobarbituric acid reactive substances and apoptosis in DLD-1 colorectal adenocarcinoma cells. It also inhibits prostaglandin biosynthesis in sheep vesicular gland microsomes.

Chemical Structure

Calendic Acid

CAS#5204-87-5

Theoretical Analysis

MedKoo Cat#: 462943

Name: Calendic Acid

CAS#: 5204-87-5

Chemical Formula: C18H30O2

Exact Mass: 278.2246

Molecular Weight: 278.44

Elemental Analysis: C, 77.65; H, 10.86; O, 11.49

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 285.00	Back order
5mg	USD 750.00	Back order

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Related CAS #

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Synonym

α-Calendic Acid; Calendulic Acid; trans,trans,cis-8,10,12-Octadecatrienoic Acid; 8(E),10(E),12(Z)-Octadecatrienoic Acid;

IUPAC/Chemical Name

(8E,10E,12Z)-octadeca-8,10,12-trienoic acid

InChi Key

DQGMPXYVZZCNDQ-KBPWROHVSA-N

InChi Code

InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-11H,2-5,12-17H2,1H3,(H,19,20)/b7-6-,9-8+,11-10+

SMILES Code

OC(CCCCCC/C=C/C=C/C=C\CCCCC)=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

>3 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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 278.44 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

1: Garaiova M, Hua Q, Holic R. Heterologous Production of Calendic Acid Naturally Found in Calendula officinalis by Recombinant Fission Yeast. J Agric Food Chem. 2023 Mar 1;71(8):3842-3851. doi: 10.1021/acs.jafc.2c08967. Epub 2023 Feb 16. PMID: 36795330. 2: Li Q, Wang H, Ye S, Xiao S, Xie Y, Liu X, Wang J. Induction of apoptosis and inhibition of invasion in choriocarcinoma JEG-3 cells by α-calendic acid and β-calendic acid. Prostaglandins Leukot Essent Fatty Acids. 2013 Oct;89(5):367-76. doi: 10.1016/j.plefa.2013.06.007. Epub 2013 Aug 14. PMID: 24035100. 3: Cahoon EB, Ripp KG, Hall SE, Kinney AJ. Formation of conjugated delta8,delta10-double bonds by delta12-oleic-acid desaturase-related enzymes: biosynthetic origin of calendic acid. J Biol Chem. 2001 Jan 26;276(4):2637-43. doi: 10.1074/jbc.M009188200. Epub 2000 Nov 6. PMID: 11067856. 4: Dhar Dubey KK, Sharma G, Kumar A. Conjugated Linolenic Acids: Implication in Cancer. J Agric Food Chem. 2019 Jun 5;67(22):6091-6101. doi: 10.1021/acs.jafc.9b01379. Epub 2019 May 23. PMID: 31070027. 5: Dulf FV, Pamfil D, Baciu AD, Pintea A. Fatty acid composition of lipids in pot marigold (Calendula officinalis L.) seed genotypes. Chem Cent J. 2013 Jan 17;7(1):8. doi: 10.1186/1752-153X-7-8. PMID: 23327299; PMCID: PMC3560196. 6: Fritsche K, Hornung E, Peitzsch N, Renz A, Feussner I. Isolation and characterization of a calendic acid producing (8,11)-linoleoyl desaturase. FEBS Lett. 1999 Dec 3;462(3):249-53. doi: 10.1016/s0014-5793(99)01541-0. PMID: 10622705. 7: Chisholm MJ, Hopkins CY. Calendic acid in seed oils of the genus Calendula. Can J Biochem. 1967 Feb;45(2):251-4. doi: 10.1139/o67-028. PMID: 6021179. 8: Yasui Y, Hosokawa M, Kohno H, Tanaka T, Miyashita K. Growth inhibition and apoptosis induction by all-trans-conjugated linolenic acids on human colon cancer cells. Anticancer Res. 2006 May-Jun;26(3A):1855-60. PMID: 16827117. 9: Metzger JO, Bornscheuer U. Lipids as renewable resources: current state of chemical and biotechnological conversion and diversification. Appl Microbiol Biotechnol. 2006 Jun;71(1):13-22. doi: 10.1007/s00253-006-0335-4. Epub 2006 Apr 8. PMID: 16604360. 10: Reed DW, Savile CK, Qiu X, Buist PH, Covello PS. Mechanism of 1,4-dehydrogenation catalyzed by a fatty acid (1,4)-desaturase of Calendula officinalis. Eur J Biochem. 2002 Oct;269(20):5024-9. doi: 10.1046/j.1432-1033.2002.03209.x. PMID: 12383261. 11: Mashhadi Z, Boeglin WE, Brash AR. Robust inhibitory effects of conjugated linolenic acids on a cyclooxygenase-related linoleate 10S-dioxygenase: Comparison with COX-1 and COX-2. Biochim Biophys Acta. 2015 Oct;1851(10):1346-52. doi: 10.1016/j.bbalip.2015.07.004. Epub 2015 Jul 21. PMID: 26209563; PMCID: PMC4561586. 12: Qiu X, Reed DW, Hong H, MacKenzie SL, Covello PS. Identification and analysis of a gene from Calendula officinalis encoding a fatty acid conjugase. Plant Physiol. 2001 Feb;125(2):847-55. doi: 10.1104/pp.125.2.847. PMID: 11161042; PMCID: PMC64886. 13: Chardigny JM, Hasselwander O, Genty M, Kraemer K, Ptock A, Sébédio JL. Effect of conjugated FA on feed intake, body composition, and liver FA in mice. Lipids. 2003 Sep;38(9):895-902. doi: 10.1007/s11745-003-1142-5. PMID: 14584596. 14: Cahoon EB, Dietrich CR, Meyer K, Damude HG, Dyer JM, Kinney AJ. Conjugated fatty acids accumulate to high levels in phospholipids of metabolically engineered soybean and Arabidopsis seeds. Phytochemistry. 2006 Jun;67(12):1166-76. doi: 10.1016/j.phytochem.2006.04.013. Epub 2006 Jun 9. PMID: 16762380.