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MedKoo Cat#: 463151 | Name: Papyracillic acid A

Description:

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

Papyracillic acid A is a natural inducer of accumulation of reactive oxygen species in nutrient-deprived cancer cells, exhibiting preferential cytotoxicity to human pancreatic cancer cells under nutrient-deprived compared with nutrient-sufficient conditions.

Chemical Structure

Papyracillic acid A
Papyracillic acid A
CAS#960148-59-82

Theoretical Analysis

MedKoo Cat#: 463151

Name: Papyracillic acid A

CAS#: 960148-59-82

Chemical Formula: C11H14O5

Exact Mass: 226.0841

Molecular Weight: 226.23

Elemental Analysis: C, 58.40; H, 6.24; O, 35.36

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
Papyracillic acid A;
IUPAC/Chemical Name
(5S,7R,8S)-7-hydroxy-4-methoxy-7,8-dimethyl-9-methylene-1,6-dioxaspiro[4.4]non-3-en-2-one
InChi Key
UEYMIBGYKZFDMD-MQOMDTIOSA-N
InChi Code
InChI=1S/C11H14O5/c1-6-7(2)11(16-10(6,3)13)8(14-4)5-9(12)15-11/h5-6,13H,2H2,1,3-4H3/t6-,10+,11+/m0/s1
SMILES Code
C[C@@H]1[C@@](O)(C)O[C@]2(OC(C=C2OC)=O)C1=C
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

Preparing Stock Solutions

The following data is based on the product molecular weight 226.23 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: Onodera T, Momose I, Adachi H, Yamazaki Y, Sawa R, Ohba SI, Kawada M. Human pancreatic cancer cells under nutrient deprivation are vulnerable to redox system inhibition. J Biol Chem. 2020 Sep 25:jbc.RA120.013893. doi: 10.1074/jbc.RA120.013893. Epub ahead of print. PMID: 32978257. 2: Cimmino A, Andolfi A, Avolio F, Ali A, Tabanca N, Khan IA, Evidente A. Cyclopaldic acid, seiridin, and sphaeropsidin A as fungal phytotoxins, and larvicidal and biting deterrents against Aedes aegypti (Diptera: Culicidae): structure-activity relationships. Chem Biodivers. 2013 Jul;10(7):1239-51. doi: 10.1002/cbdv.201200358. Erratum in: Chem Biodivers. 2013 Dec;10(12):2302. PMID: 23847068. 3: Mazzone JR, Zercher CK. Syntheses of papyracillic acids: application of the tandem chain extension-acylation reaction. J Org Chem. 2012 Oct 19;77(20):9171-8. doi: 10.1021/jo3017617. Epub 2012 Oct 5. PMID: 23013246; PMCID: PMC3477294. 4: Evidente A, Berestetskiy A, Cimmino A, Tuzi A, Superchi S, Melck D, Andolfi A. Papyracillic acid, a phytotoxic 1,6-dioxaspiro[4,4]nonene produced by Ascochyta agropyrina Var. nana, a potential mycoherbicide for Elytrigia repens biocontrol. J Agric Food Chem. 2009 Dec 9;57(23):11168-73. doi: 10.1021/jf903499y. PMID: 19891481.