MedKoo Cat#: 208492 | Name: Pisatin

Description:

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

Pisatin was shown to have two distinct inhibitory effects on amoebae of the cellular slime mould Dictyostelium discoideum. One effect was cytolytic and was demonstrable even in non-growing cells whereas the second effect was observed only under conditions favourable to growth.

Chemical Structure

Pisatin
Pisatin
CAS#469-01-2

Theoretical Analysis

MedKoo Cat#: 208492

Name: Pisatin

CAS#: 469-01-2

Chemical Formula: C17H14O6

Exact Mass: 314.0790

Molecular Weight: 314.29

Elemental Analysis: C, 64.97; H, 4.49; O, 30.54

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
UNII-V6L86DZ4N3
IUPAC/Chemical Name
6H-(1,3)Dioxolo(5,6)benzofuro(3,2-c)(1)benzopyran-6a(12aH)-ol, 3-methoxy-, (6aR-cis)-
InChi Key
LZMRDTLRSDRUSU-SJORKVTESA-N
InChi Code
InChI=1S/C17H14O6/c1-19-9-2-3-10-12(4-9)20-7-17(18)11-5-14-15(22-8-21-14)6-13(11)23-16(10)17/h2-6,16,18H,7-8H2,1H3/t16-,17+/m1/s1
SMILES Code
O[C@]12COC3=CC(OC)=CC=C3[C@@]1([H])OC4=CC(OCO5)=C5C=C42
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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 314.29 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: Celoy RM, VanEtten HD. (+)-Pisatin biosynthesis: from (-) enantiomeric intermediates via an achiral 7,2'-dihydroxy-4',5'-methylenedioxyisoflav-3-ene. Phytochemistry. 2014 Feb;98:120-7. doi: 10.1016/j.phytochem.2013.10.017. Epub 2013 Dec 9. PMID: 24332213. 2: Wasmann CC, Coleman JJ. Screening and Assessment of Pisatin Demethylase Activity (PDA ). Methods Mol Biol. 2022;2391:185-190. doi: 10.1007/978-1-0716-1795-3_15. PMID: 34686986. 3: Papavinasasundaram KG, Kasbekar DP. Pisatin resistance in Dictyostelium discoideum and Neurospora crassa: comparison of mutant phenotypes. J Gen Microbiol. 1993 Dec;139(12):3035-41. doi: 10.1099/00221287-139-12-3035. PMID: 8126430. 4: Uchida K, Aoki T, Suzuki H, Akashi T. Molecular cloning and biochemical characterization of isoflav-3-ene synthase, a key enzyme of the biosyntheses of (+)-pisatin and coumestrol. Plant Biotechnol (Tokyo). 2020 Sep 25;37(3):301-310. doi: 10.5511/plantbiotechnology.20.0421a. PMID: 33088193; PMCID: PMC7557667. 5: Matthews DE, Van Etten HD. Detoxification of the phytoalexin pisatin by a fungal cytochrome P-450. Arch Biochem Biophys. 1983 Jul 15;224(2):494-505. doi: 10.1016/0003-9861(83)90237-0. PMID: 6870275. 6: Borejsza-Wysocki W, Borejsza-Wysocka E, Hrazdina G. Pisatin metabolism in pea (Pisum sativum L.) cell suspension cultures. Plant Cell Rep. 1997 Feb;16(5):304-309. doi: 10.1007/BF01088286. PMID: 30727668. 7: DiCenzo GL, VanEtten HD. Studies on the late steps of (+) pisatin biosynthesis: evidence for (-) enantiomeric intermediates. Phytochemistry. 2006 Apr;67(7):675-83. doi: 10.1016/j.phytochem.2005.12.027. Epub 2006 Feb 28. PMID: 16504226. 8: PERRIN DR, BOTTOMLEY W. Pisatin: an antifungal substance from Pisum sativum L. Nature. 1961 Jul 1;191:76-7. doi: 10.1038/191076a0. PMID: 13734533. 9: Wu Q, VanEtten HD. Introduction of plant and fungal genes into pea (Pisum sativum L.) hairy roots reduces their ability to produce pisatin and affects their response to a fungal pathogen. Mol Plant Microbe Interact. 2004 Jul;17(7):798-804. doi: 10.1094/MPMI.2004.17.7.798. PMID: 15242174. 10: Sweigard JA, Matthews DE, Vanetten HD. Synthesis of the phytoalexin pisatin by a methyltransferase from pea. Plant Physiol. 1986 Jan;80(1):277-9. doi: 10.1104/pp.80.1.277. PMID: 16664598; PMCID: PMC1075096.