MedKoo Cat#: 598195 | Name: Laccaic acid A

Description:

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

Laccaic acid A is a direct, DNA-competitive inhibitor of DNA methyltransferase 1.

Chemical Structure

Laccaic acid A
Laccaic acid A
CAS#15979-35-8

Theoretical Analysis

MedKoo Cat#: 598195

Name: Laccaic acid A

CAS#: 15979-35-8

Chemical Formula: C26H19NO12

Exact Mass: 537.0907

Molecular Weight: 537.43

Elemental Analysis: C, 58.11; H, 3.56; N, 2.61; O, 35.72

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
Bulk Inquiry
Related CAS #
No Data
Synonym
Laccaic acid A;
IUPAC/Chemical Name
7-(5-(2-acetamidoethyl)-2-hydroxyphenyl)-3,5,6,8-tetrahydroxy-9,10-dioxo-9,10-dihydroanthracene-1,2-dicarboxylic acid
InChi Key
IHLWXZNPOVMUFQ-UHFFFAOYSA-N
InChi Code
InChI=1S/C26H19NO12/c1-8(28)27-5-4-9-2-3-12(29)10(6-9)15-22(33)19-18(24(35)23(15)34)20(31)11-7-13(30)16(25(36)37)17(26(38)39)14(11)21(19)32/h2-3,6-7,29-30,33-35H,4-5H2,1H3,(H,27,28)(H,36,37)(H,38,39)
SMILES Code
O=C1c2c(C(c3c1c(C(O)=O)c(C(O)=O)c(O)c3)=O)c(O)c(O)c(c4cc(CCNC(C)=O)ccc4O)c2O
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 537.43 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.

Recalculate based on batch purity %
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: Fagan RL, Cryderman DE, Kopelovich L, Wallrath LL, Brenner C. Laccaic acid A is a direct, DNA-competitive inhibitor of DNA methyltransferase 1. J Biol Chem. 2013 Aug 16;288(33):23858-67. doi: 10.1074/jbc.M113.480517. Epub 2013 Jul 9. PubMed PMID: 23839987; PubMed Central PMCID: PMC3745332. 2: Dokmaisrijan S, Payaka A, Tantishaiyakul V, Chairat M, Nimmanpipug P, Lee VS. Conformations and spectroscopic properties of laccaic acid A in the gas phase and in implicit water. Spectrochim Acta A Mol Biomol Spectrosc. 2013 Mar 15;105:125-34. doi: 10.1016/j.saa.2012.11.105. Epub 2012 Dec 13. PubMed PMID: 23295218. 3: Sekido C, Nishimura N, Takai M, Hasumi K. Inhibition of plasma hyaluronan-binding protein autoactivation by laccaic acid. Biosci Biotechnol Biochem. 2010;74(11):2320-2. Epub 2010 Nov 7. PubMed PMID: 21071862. 4: Dube DK, Loch-Caruso R, Trosko JE, Chakravarty I, Ghosh A, Loeb LA. Assessment of the carcinogenic potential of a proposed food coloring additive, laccaic acid, using short-term assays. Cell Biol Toxicol. 1984 Oct;1(1):111-25. PubMed PMID: 6401125. 5: Nishizaki Y, Ishizuki K, Akiyama H, Tada A, Sugimoto N, Sato K. Preparation of a Ammonia-Treated Lac Dye and Structure Elucidation of Its Main Component. Shokuhin Eiseigaku Zasshi. 2016;57(6):193-200. doi: 10.3358/shokueishi.57.193. PubMed PMID: 28025453. 6: Sako F, Kobayashi N, Watabe H, Yokosawa N, Taniguchi N. Induction of gamma-glutamyl transpeptidase and glutathione S-transferase in cultured fetal rat hepatocytes by laccaic acid and monascus pigments. Chem Biol Interact. 1983 Apr-May;44(1-2):17-26. PubMed PMID: 6133634. 7: Hirata K, Uematsu Y, Suzuki K, Iida K, Yasuda K, Saito K. [Analysis of main pigments and other ingredients in lac color product]. Shokuhin Eiseigaku Zasshi. 2001 Apr;42(2):109-13. Japanese. PubMed PMID: 11486376. 8: Shamim G, Ranjan SK, Pandey DM, Sharma KK, Ramani R. Lac dye as a potential anti-neoplastic agent. J Cancer Res Ther. 2016 Apr-Jun;12(2):1033-5. doi: 10.4103/0973-1482.155975. PubMed PMID: 27461693. 9: Kemmochi S, Yamamichi S, Shimamoto K, Onda N, Hasumi K, Suzuki K, Mitsumori K, Shibutani M. Lac color inhibits development of rat thyroid carcinomas through targeting activation of plasma hyaluronan-binding protein. Exp Biol Med (Maywood). 2012 Jun;237(6):728-38. doi: 10.1258/ebm.2012.011319. Epub 2012 Jun 19. PubMed PMID: 22715430. 10: Hirata K, Uematsu Y, Suzuki K, Iida K, Kamata K. [Analysis of lac color in diets and feces of rats for toxicity studies]. Shokuhin Eiseigaku Zasshi. 2002 Apr;43(2):110-3. Japanese. PubMed PMID: 12092412. 11: Oka H, Ito Y, Yamada S, Kagami T, Hayakawa J, Harada K, Atsumi E, Suzuki M, Suzuki M, Odani H, Akahori S, Maeda K, Nakazawa H, Ito Y. Separation of lac dye components by high-speed counter-current chromatography. J Chromatogr A. 1998 Jul 10;813(1):71-7. PubMed PMID: 9697316. 12: Zwergel C, Valente S, Mai A. DNA Methyltransferases Inhibitors from Natural Sources. Curr Top Med Chem. 2016;16(7):680-96. Review. PubMed PMID: 26303417. 13: Yoshida A, Takagaki Y, Nishimune T. Enzyme immunoassay for carminic acid in foods. J AOAC Int. 1995 May-Jun;78(3):807-11. PubMed PMID: 7756895. 14: Puchalska M, Orlińska M, Ackacha MA, Połeć-Pawlak K, Jarosz M. Identification of anthraquinone coloring matters in natural red dyes by electrospray mass spectrometry coupled to capillary electrophoresis. J Mass Spectrom. 2003 Dec;38(12):1252-8. PubMed PMID: 14696204. 15: Yamada S, Noda N, Mikami E, Hayakawa J, Yamada M. Analysis of natural coloring matters in food. III. Application of methylation with diazomethane for the detection of lac color. J Assoc Off Anal Chem. 1989 Jan-Feb;72(1):48-51. PubMed PMID: 2715136. 16: Xu N, Shi YN, Zhong X, Cao Y, Wang L, Jia TZ. A new saikogenin from the roots of Bupleurum bicaule. Chin J Nat Med. 2014 Apr;12(4):305-8. doi: 10.1016/S1875-5364(14)60060-1. PubMed PMID: 24863358. 17: Banerjee TS, Bhaumik G, Yu CL, Swaminathan B, Giri AK, Srivastava S, Bhattacharjee SB. Evaluation of the genotoxicity of lac dye. Food Chem Toxicol. 1984 Aug;22(8):677-9. PubMed PMID: 6381266. 18: Kuramoto Y, Yamada K, Tsuruta O, Sugano M. Effect of natural food colorings on immunoglobulin production in vitro by rat spleen lymphocytes. Biosci Biotechnol Biochem. 1996 Oct;60(10):1712-3. PubMed PMID: 8987673. 19: Maguregui MI, Alonso RM, Barandiaran M, Jimenez RM, García N. Micellar electrokinetic chromatography method for the determination of several natural red dyestuff and lake pigments used in art work. J Chromatogr A. 2007 Jun 22;1154(1-2):429-36. Epub 2007 Mar 30. PubMed PMID: 17452040. 20: Hawas UW, El-Ansari MA, Laatsch H. A new alpha-methylanthraquinone glucoside from Emex spinosus. Nat Prod Res. 2006 Jul 10;20(8):742-7. PubMed PMID: 16753907.