Papyracillic acid A

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MedKoo CAT#: 463151

CAS#: 960148-59-82

Description: 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

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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: 226.08
Molecular Weight: 226.228
Elemental Analysis: C, 58.40; H, 6.24; O, 35.36

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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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:

Biological target:
In vitro activity:
In vivo activity:

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.