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MedKoo Cat#: 140100 | Name: Pericosine A

Description:

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

Pericosine A is a fungal and marine metabolite with antitumor activity and skunk odor-neutralizing properties

Chemical Structure

Pericosine A
CAS#200335-68-8

Theoretical Analysis

MedKoo Cat#: 140100

Name: Pericosine A

CAS#: 200335-68-8

Chemical Formula: C8H11ClO5

Exact Mass: 222.0295

Molecular Weight: 222.62

Elemental Analysis: C, 43.16; H, 4.98; Cl, 15.92; O, 35.93

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 #
200335-69-9
Synonym
Pericosine, Pericosine B, Pericosine C, Pericosine D, Pericosine E
IUPAC/Chemical Name
(3S,4S,5S,6S)-6-chloro-3,4,5-trihydroxy-1-cyclohexene-1-carboxylic acid, methyl ester
InChi Key
AEDMWQPFIPNFCS-ZTYPAOSTSA-N
InChi Code
InChI=1S/C8H11ClO5/c1-14-8(13)3-2-4(10)6(11)7(12)5(3)9/h2,4-7,10-12H,1H3/t4-,5-,6-,7+/m0/s1
SMILES Code
O[C@H]1C=C(C(OC)=O)[C@H](Cl)[C@@H](O)[C@H]1O
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 222.62 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: Usami Y, Mizobuchi Y, Ijuin M, Yamada T, Morita M, Mizuki K, Yoneyama H, Harusawa S. Synthesis of 6-Halo-Substituted Pericosine A and an Evaluation of Their Antitumor and Antiglycosidase Activities. Mar Drugs. 2022 Jun 30;20(7):438. doi: 10.3390/md20070438. PMID: 35877731; PMCID: PMC9323573. 2: Usami Y, Nakamura K, Mizobuchi Y, Mizuki K, Harusawa S, Yoneyama H, Yamada T. Enantiomeric composition of natural pericosine A derived from Periconia byssoides and α-glycosidase inhibitory activity of (-)-enantiomer. Chirality. 2022 Oct;34(10):1320-1327. doi: 10.1002/chir.23491. Epub 2022 Jul 1. PMID: 35775430. 3: Du L, Munteanu C, King JB, Frantz DE, Cichewicz RH. An Electrophilic Natural Product Provides a Safe and Robust Odor Neutralization Approach To Counteract Malodorous Organosulfur Metabolites Encountered in Skunk Spray. J Nat Prod. 2019 Jul 26;82(7):1989-1999. doi: 10.1021/acs.jnatprod.9b00415. Epub 2019 Jul 5. PMID: 31273979. 4: Usami Y, Ohsugi M, Mizuki K, Ichikawa H, Arimoto M. Facile and efficient synthesis of naturally occurring carbasugars (+)-pericosines A and C. Org Lett. 2009 Jun 18;11(12):2699-701. doi: 10.1021/ol9008188. PMID: 19514797. 5: Du L, You J, Nicholas KM, Cichewicz RH. Chemoreactive Natural Products that Afford Resistance Against Disparate Antibiotics and Toxins. Angew Chem Int Ed Engl. 2016 Mar 18;55(13):4220-5. doi: 10.1002/anie.201511348. Epub 2016 Mar 1. PMID: 26928999; PMCID: PMC4959538. 6: Usami Y, Takaoka I, Ichikawa H, Horibe Y, Tomiyama S, Ohtsuka M, Imanishi Y, Arimoto M. First total synthesis of antitumor natural product (+)- and (-)-pericosine A: determination of absolute stereo structure. J Org Chem. 2007 Aug 3;72(16):6127-34. doi: 10.1021/jo070715l. Epub 2007 Jul 12. PMID: 17628106. 7: Paredes-Gamero EJ, Nogueira-Pedro A, Miranda A, Justo GZ. Hematopoietic modulators as potential agents for the treatment of leukemia. Front Biosci (Elite Ed). 2013 Jan 1;5(1):130-40. doi: 10.2741/e602. PMID: 23276976. 8: Yamada T, Iritani M, Ohishi H, Tanaka K, Minoura K, Doi M, Numata A. Pericosines, antitumour metabolites from the sea hare-derived fungus Periconia byssoides. Structures and biological activities. Org Biomol Chem. 2007 Dec 21;5(24):3979-86. doi: 10.1039/b713060k. Epub 2007 Oct 26. PMID: 18043803. 9: Boyd DR, Sharma ND, Acaru CA, Malone JF, O'Dowd CR, Allen CC, Stevenson PJ. Chemoenzymatic synthesis of carbasugars (+)-pericosines A-C from diverse aromatic cis-dihydrodiol precursors. Org Lett. 2010 May 21;12(10):2206-9. doi: 10.1021/ol100525r. PMID: 20411952. 10: Usami Y, Ichikawa H, Arimoto M. Synthetic efforts for stereo structure determination of cytotoxic marine natural product pericosines as metabolites of Periconia sp. from sea hare. Int J Mol Sci. 2008 Mar;9(3):401-421. doi: 10.3390/ijms9030401. Epub 2008 Mar 24. PMID: 19325758; PMCID: PMC2635666. 11: Tripathi S, Shaikh AC, Chen C. Facile carbohydrate-based stereocontrolled divergent synthesis of (+)-pericosines A and B. Org Biomol Chem. 2011 Nov 7;9(21):7306-8. doi: 10.1039/c1ob06383a. Epub 2011 Sep 14. PMID: 21915422.