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MedKoo Cat#: 412864 | Name: Cleistanthin

Description:

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

Cleistanthin is a member of the class of cleistanthins that is the 4-O-3,4-di-O-methyl-beta-D-xylopyranoside of 1,3-dihydronaphtho[2,3-c]furan-4-ol which is substituted by an oxo group at position 1, methoxy groups at positions 6 and 7, and a 1,3-benzodioxol-5-yl group at position 9. It is one of the toxic principles in Cleistanthus collinus. It has a role as an antihypertensive agent, an alpha-adrenergic antagonist and a diuretic. It is a xylose derivative and a member of cleistanthins.

Chemical Structure

Cleistanthin
Cleistanthin
CAS#25047-48-7

Theoretical Analysis

MedKoo Cat#: 412864

Name: Cleistanthin

CAS#: 25047-48-7

Chemical Formula: C28H28O11

Exact Mass: 540.1632

Molecular Weight: 540.52

Elemental Analysis: C, 62.22; H, 5.22; O, 32.56

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 #
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Synonym
Cleistanthin; BRN5194207; BRN-5194207; BRN 5194207
IUPAC/Chemical Name
9-(benzo[d][1,3]dioxol-5-yl)-4-((3-hydroxy-4,5-dimethoxytetrahydro-2H-pyran-2-yl)oxy)-6,7-dimethoxynaphtho[2,3-c]furan-1(3H)-one
InChi Key
FCOQWUOWHWHTJP-UHFFFAOYSA-N
InChi Code
InChI=1S/C28H28O11/c1-31-18-8-14-15(9-19(18)32-2)25(39-28-24(29)26(34-4)21(33-3)11-36-28)16-10-35-27(30)23(16)22(14)13-5-6-17-20(7-13)38-12-37-17/h5-9,21,24,26,28-29H,10-12H2,1-4H3
SMILES Code
COC1COC(C(C1OC)O)Oc(c(COC2=O)c2c3c4cc5c(OCO5)cc4)c6c3cc(OC)c(OC)c6
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

Preparing Stock Solutions

The following data is based on the product molecular weight 540.52 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: Liu S, Wang L, Ding W, Wang D, Wang X, Luo Q, Lu Y, Zhu L. Cleistanthin A inhibits the invasion of MDA-MB-231 human breast cancer cells: involvement of the β-catenin pathway. Pharmacol Rep. 2020 Feb;72(1):188-198. doi: 10.1007/s43440-019-00012-1. Epub 2019 Dec 19. PMID: 32016834. 2: Jearawuttanakul K, Khumkhrong P, Suksen K, Reabroi S, Munyoo B, Tuchinda P, Borwornpinyo S, Boonmuen N, Chairoungdua A. Cleistanthin A induces apoptosis and suppresses motility of colorectal cancer cells. Eur J Pharmacol. 2020 Dec 15;889:173604. doi: 10.1016/j.ejphar.2020.173604. Epub 2020 Sep 25. PMID: 32980346. 3: Thummar VR, Parasuraman S, Basu D, Raveendran R. Evaluation of in vivo antitumor activity of cleistanthin B in Swiss albino mice. J Tradit Complement Med. 2015 Sep 3;6(4):383-388. doi: 10.1016/j.jtcme.2015.08.004. PMID: 27774423; PMCID: PMC5067870. 4: Zhao Y, Zhang R, Lu Y, Ma J, Zhu L. Synthesis and bioevaluation of heterocyclic derivatives of Cleistanthin-A. Bioorg Med Chem. 2015 Aug 1;23(15):4884-4890. doi: 10.1016/j.bmc.2015.05.033. Epub 2015 May 27. PMID: 26059594. 5: Parasuraman S, Raveendran R, Rajesh NG, Nandhakumar S. Sub-chronic toxicological evaluation of cleistanthin A and cleistanthin B from the leaves of Cleistanthus collinus (Roxb.). Toxicol Rep. 2014 Aug 19;1:596-611. doi: 10.1016/j.toxrep.2014.08.006. PMID: 28962273; PMCID: PMC5598356. 6: Pan S, Cai H, Gu L, Cao S. Cleistanthin A inhibits the invasion and metastasis of human melanoma cells by inhibiting the expression of matrix metallopeptidase-2 and -9. Oncol Lett. 2017 Nov;14(5):6217-6223. doi: 10.3892/ol.2017.6917. Epub 2017 Sep 8. PMID: 29113270; PMCID: PMC5661418. 7: Pradheepkumar CP, Panneerselvam N, Shanmugam G. Cleistanthin A causes DNA strand breaks and induces apoptosis in cultured cells. Mutat Res. 2000 Jan 24;464(2):185-93. doi: 10.1016/s1383-5718(99)00179-5. PMID: 10648905. 8: Parasuraman S, Raveendran R. Effect of cleistanthin A and B on adrenergic and cholinergic receptors. Pharmacogn Mag. 2011 Jul;7(27):243-7. doi: 10.4103/0973-1296.84239. PMID: 21969796; PMCID: PMC3173900. 9: Parasuraman S, Raveendran R. Diuretic effects of cleistanthin a and cleistanthin B from the leaves of cleistanthus collinus in wistar rats. J Young Pharm. 2012 Apr;4(2):73-7. doi: 10.4103/0975-1483.96616. PMID: 22754257; PMCID: PMC3385220. 10: Zhao Y, Lu Y, Ma J, Zhu L. Synthesis and Evaluation of Cleistanthin A Derivatives as Potent Vacuolar H(+) -ATPase Inhibitors. Chem Biol Drug Des. 2015 Oct;86(4):691-6. doi: 10.1111/cbdd.12538. Epub 2015 Mar 13. PMID: 25677205.