Monocrotalic acid | CAS#26543-09-9 | byproducer of dehydromonocrotaline

MedKoo Cat#: 596859 | Name: Monocrotalic acid

Description:

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

Monocrotalic acid is a stable byproducer of dehydromonocrotaline reacting with cellular nucleophiles and indicates the amount of monocrotaline dehydrogenation when carboxylesterase activity is negligible.

Chemical Structure

Monocrotalic acid

CAS#26543-09-9

Theoretical Analysis

MedKoo Cat#: 596859

Name: Monocrotalic acid

CAS#: 26543-09-9

Chemical Formula: C8H12O5

Exact Mass: 188.0685

Molecular Weight: 188.17

Elemental Analysis: C, 51.06; H, 6.43; O, 42.51

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 #

No Data

Synonym

Monocrotalic acid;

IUPAC/Chemical Name

(2R,3R,4R)-3-hydroxy-2,3,4-trimethyl-5-oxotetrahydrofuran-2-carboxylic acid

InChi Key

YTEPYGBARSCSMX-NETWJXFUSA-N

InChi Code

InChI=1S/C8H12O5/c1-4-5(9)13-8(3,6(10)11)7(4,2)12/h4,12H,1-3H3,(H,10,11)/t4-,7+,8-/m0/s1

SMILES Code

O=C([C@]([C@](C)(O)[C@H]1C)(C)OC1=O)O

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 188.17 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.

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: Reid MJ, Lamé MW, Morin D, Wilson DW, Segall HJ. Monocrotaline metabolism and distribution in Fisher 344 and Sprague-Dawley rats. Comp Biochem Physiol B Biochem Mol Biol. 1997 May;117(1):115-23. PubMed PMID: 9180020. 2: Lamé MW, Jones AD, Morin D, Segall HJ. Metabolism of [14C]monocrotaline by isolated perfused rat liver. Drug Metab Dispos. 1991 Mar-Apr;19(2):516-24. PubMed PMID: 1676664. 3: Winter CK, Segall HJ, Jones AD. Determination of pyrrolizidine alkaloid metabolites from mouse liver microsomes using tandem mass spectrometry and gas chromatography/mass spectrometry. Biomed Environ Mass Spectrom. 1988 Mar 1;15(5):265-73. PubMed PMID: 3365497. 4: Lafranconi WM, Ohkuma S, Huxtable RJ. Biliary excretion of novel pneumotoxic metabolites of the pyrrolizidine alkaloid, monocrotaline. Toxicon. 1985;23(6):983-92. PubMed PMID: 3938082. 5: Robins DJ, Bale NM, Crout DH. Pyrrolizidine alkaloids. Biosynthesis of monocrotalic acid, the necic acid component of monocrotaline. J Chem Soc Perkin 1. 1974;0(18):2082-6. PubMed PMID: 4473457. 6: Robins DJ, Crout HG. Pyrrolizidine alkaloids. The absolute configuration at C-2 in monocrotalic acid. J Chem Soc Perkin 1. 1970;9:1334-6. PubMed PMID: 5463837.