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MedKoo Cat#: 461787 | Name: Sappanchalcone

Description:

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

Sappanchalcone is a bioactive flavonoid isolated from the heartwood of Caesalpinia sappan L. that possesses anti-inflammatory effects.

Chemical Structure

Sappanchalcone
Sappanchalcone
CAS#94344-54-4

Theoretical Analysis

MedKoo Cat#: 461787

Name: Sappanchalcone

CAS#: 94344-54-4

Chemical Formula: C16H14O5

Exact Mass: 286.0841

Molecular Weight: 286.28

Elemental Analysis: C, 67.13; H, 4.93; O, 27.94

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.
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Related CAS #
No Data
Synonym
Sappanchalcone;
IUPAC/Chemical Name
(E)-3-(3,4-dihydroxyphenyl)-1-(4-hydroxy-2-methoxyphenyl)prop-2-en-1-one
InChi Key
JVGNTXGHBHMJDO-QHHAFSJGSA-N
InChi Code
InChI=1S/C16H14O5/c1-21-16-9-11(17)4-5-12(16)13(18)6-2-10-3-7-14(19)15(20)8-10/h2-9,17,19-20H,1H3/b6-2+
SMILES Code
O=C(C1=CC=C(O)C=C1OC)/C=C/C2=CC=C(O)C(O)=C2
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 286.28 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: Jung EG, Han KI, Kwon HJ, Patnaik BB, Kim WJ, Hur GM, Nam KW, Han MD. Anti-inflammatory activity of sappanchalcone isolated from Caesalpinia sappan L. in a collagen-induced arthritis mouse model. Arch Pharm Res. 2015 Jun;38(6):973-83. doi: 10.1007/s12272-015-0557-z. Epub 2015 Jan 14. PubMed PMID: 25586964. 2: Jeong GS, Lee DS, Li B, Lee HJ, Kim EC, Kim YC. Effects of sappanchalcone on the cytoprotection and anti-inflammation via heme oxygenase-1 in human pulp and periodontal ligament cells. Eur J Pharmacol. 2010 Oct 10;644(1-3):230-7. doi: 10.1016/j.ejphar.2010.06.059. Epub 2010 Jul 13. PubMed PMID: 20621084. 3: Lee YM, Kim YC, Choi BJ, Lee DW, Yoon JH, Kim EC. Mechanism of sappanchalcone-induced growth inhibition and apoptosis in human oral cancer cells. Toxicol In Vitro. 2011 Dec;25(8):1782-8. doi: 10.1016/j.tiv.2011.09.009. Epub 2011 Sep 19. PubMed PMID: 21963806. 4: Tewtrakul S, Tungcharoen P, Sudsai T, Karalai C, Ponglimanont C, Yodsaoue O. Antiinflammatory and Wound Healing Effects of Caesalpinia sappan L. Phytother Res. 2015 Jun;29(6):850-6. doi: 10.1002/ptr.5321. Epub 2015 Mar 11. PubMed PMID: 25760294. 5: Zhang Q, Liu JL, Qi XM, Qi CT, Yu Q. Inhibitory activities of Lignum Sappan extractives on growth and growth-related signaling of tumor cells. Chin J Nat Med. 2014 Aug;12(8):607-12. doi: 10.1016/S1875-5364(14)60092-3. PubMed PMID: 25156286. 6: Tewtrakul S, Chaniad P, Pianwanit S, Karalai C, Ponglimanont C, Yodsaoue O. Anti-HIV-1 Integrase Activity and Molecular Docking Study of Compounds from Caesalpinia  sappan L. Phytother Res. 2015 May;29(5):724-9. doi: 10.1002/ptr.5307. Epub 2015 Feb 11. PubMed PMID: 25676492. 7: Bui TH, Nguyen NT, Dang PH, Nguyen HX, Nguyen MT. Design and synthesis of chalcone derivatives as potential non-purine xanthine oxidase inhibitors. Springerplus. 2016 Oct 13;5(1):1789. eCollection 2016. PubMed PMID: 27795931; PubMed Central PMCID: PMC5063830. 8: Sasaki Y, Suzuki M, Matsumoto T, Hosokawa T, Kobayashi T, Kamata K, Nagumo S. Vasorelaxant activity of Sappan Lignum constituents and extracts on rat aorta and mesenteric artery. Biol Pharm Bull. 2010;33(9):1555-60. PubMed PMID: 20823574. 9: Nagai M, Nagumo S, Eguchi I, Lee SM, Suzuki T. [Sappanchalcone from Caesalpinia sappan L., the proposed biosynthetic precursor of brazilin]. Yakugaku Zasshi. 1984 Sep;104(9):935-8. Japanese. PubMed PMID: 6527222. 10: Sasaki Y, Hosokawa T, Nagai M, Nagumo S. In vitro study for inhibition of NO production about constituents of Sappan Lignum. Biol Pharm Bull. 2007 Jan;30(1):193-6. PubMed PMID: 17202686. 11: Baek NI, Jeon SG, Ahn EM, Hahn JT, Bahn JH, Jang JS, Cho SW, Park JK, Choi SY. Anticonvulsant compounds from the wood of Caesalpinia sappan L. Arch Pharm Res. 2000 Aug;23(4):344-8. PubMed PMID: 10976581. 12: Moon HI, Chung IM, Seo SH, Kang EY. Protective effects of 3'-deoxy-4-O-methylepisappanol from Caesalpinia sappan against glutamate-induced neurotoxicity in primary cultured rat cortical cells. Phytother Res. 2010 Mar;24(3):463-5. doi: 10.1002/ptr.2982. PubMed PMID: 19777498. 13: Lee MJ, Lee HS, Kim H, Yi HS, Park SD, Moon HI, Park WH. Antioxidant properties of benzylchroman derivatives from Caesalpinia sappan L. against oxidative stress evaluated in vitro. J Enzyme Inhib Med Chem. 2010 Oct;25(5):608-14. doi: 10.3109/14756360903373376. Retraction in: J Enzyme Inhib Med Chem. 2012 Oct;27(5):758. PubMed PMID: 20105050. 14: Yodsaoue O, Cheenpracha S, Karalai C, Ponglimanont C, Tewtrakul S. Anti-allergic activity of principles from the roots and heartwood of Caesalpinia sappan on antigen-induced beta-hexosaminidase release. Phytother Res. 2009 Jul;23(7):1028-31. doi: 10.1002/ptr.2670. PubMed PMID: 19173220. 15: Liu AL, Shu SH, Qin HL, Lee SM, Wang YT, Du GH. In vitro anti-influenza viral activities of constituents from Caesalpinia sappan. Planta Med. 2009 Mar;75(4):337-9. doi: 10.1055/s-0028-1112208. Epub 2009 Jan 15. PubMed PMID: 19148862. 16: Fu LC, Huang XA, Lai ZY, Hu YJ, Liu HJ, Cai XL. A new 3-benzylchroman derivative from Sappan Lignum (Caesalpinia sappan). Molecules. 2008 Aug 28;13(8):1923-30. PubMed PMID: 18794793. 17: Mitani K, Takano F, Kawabata T, Allam AE, Ota M, Takahashi T, Yahagi N, Sakurada C, Fushiya S, Ohta T. Suppression of melanin synthesis by the phenolic constituents of sappanwood (Caesalpinia sappan). Planta Med. 2013 Jan;79(1):37-44. doi: 10.1055/s-0032-1327897. Epub 2012 Nov 15. PubMed PMID: 23154842. 18: van Andel T, de Boer HJ, Barnes J, Vandebroek I. Medicinal plants used for menstrual disorders in Latin America, the Caribbean, sub-Saharan Africa, South and Southeast Asia and their uterine properties: a review. J Ethnopharmacol. 2014 Sep 11;155(2):992-1000. doi: 10.1016/j.jep.2014.06.049. Epub 2014 Jun 26. Review. PubMed PMID: 24975195. 19: Nguyen MT, Awale S, Tezuka Y, Tran QL, Kadota S. Xanthine oxidase inhibitors from the heartwood of Vietnamese Caesalpinia sappan. Chem Pharm Bull (Tokyo). 2005 Aug;53(8):984-8. PubMed PMID: 16079532. 20: Washiyama M, Sasaki Y, Hosokawa T, Nagumo S. Anti-inflammatory constituents of Sappan Lignum. Biol Pharm Bull. 2009 May;32(5):941-4. PubMed PMID: 19420769.