Masoprocol tetrapivalate | CAS# 180634-64-4 | Biochemical

MedKoo Cat#: 576892 | Name: Masoprocol tetrapivalate

Description:

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

Masoprocol tetrapivalate is an ester form of nordihydroguaiaretic acid with anti-neoplastic activity. Masoprocol, also known as, meso-NDGA; meso-Nordihydroguaiaretic acid, CHX100; is a potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. The compound also inhibits formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase to a lesser extent. It also serves as an antioxidant in fats and oils.

Chemical Structure

Masoprocol tetrapivalate

CAS#180634-64-4 (pivalate)

Theoretical Analysis

MedKoo Cat#: 576892

Name: Masoprocol tetrapivalate

CAS#: 180634-64-4 (pivalate)

Chemical Formula: C38H54O8

Exact Mass: 638.3819

Molecular Weight: 638.84

Elemental Analysis: C, 71.44; H, 8.52; O, 20.04

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 #

500-38-9 (stereoisomers) 27686-84-6 (RS-isomer) 500-38-9 (NGDA) 180634-64-4 (pivalate)

Synonym

Masoprocol tetrapivalate; Meso-nordihydroguaiaretic acid tetrapivalate

IUPAC/Chemical Name

Propanoic acid, 2,2-dimethyl-, (2,3-dimethyl-1,4-butanediyl)di-4,1,2-benzenetriyl ester, (R*,S*)-

InChi Key

ABDZFVNAWRWRRN-PSWAGMNNSA-N

InChi Code

InChI=1S/C38H54O8/c1-23(19-25-15-17-27(43-31(39)35(3,4)5)29(21-25)45-33(41)37(9,10)11)24(2)20-26-16-18-28(44-32(40)36(6,7)8)30(22-26)46-34(42)38(12,13)14/h15-18,21-24H,19-20H2,1-14H3/t23-,24+

SMILES Code

C[C@H](Cc1ccc(OC(=O)C(C)(C)C)c(OC(=O)C(C)(C)C)c1)[C@@H](C)Cc2ccc(OC(=O)C(C)(C)C)c(OC(=O)C(C)(C)C)c2

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

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 638.84 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: Gowri MS, Azhar RK, Kraemer FB, Reaven GM, Azhar S. Masoprocol decreases rat lipolytic activity by decreasing the phosphorylation of HSL. Am J Physiol Endocrinol Metab. 2000 Sep;279(3):E593-600. doi: 10.1152/ajpendo.2000.279.3.E593. PMID: 10950827. 2: Scribner KA, Gadbois TM, Gowri M, Azhar S, Reaven GM. Masoprocol decreases serum triglyceride concentrations in rats with fructose-induced hypertriglyceridemia. Metabolism. 2000 Sep;49(9):1106-10. doi: 10.1053/meta.2000.8604. PMID: 11016888. 3: Olsen EA, Abernethy ML, Kulp-Shorten C, Callen JP, Glazer SD, Huntley A, McCray M, Monroe AB, Tschen E, Wolf JE Jr. A double-blind, vehicle-controlled study evaluating masoprocol cream in the treatment of actinic keratoses on the head and neck. J Am Acad Dermatol. 1991 May;24(5 Pt 1):738-43. doi: 10.1016/0190-9622(91)70113-g. PMID: 1869646. 4: Cui Q, Du R, Liu M, Rong L. Lignans and Their Derivatives from Plants as Antivirals. Molecules. 2020 Jan 1;25(1):183. doi: 10.3390/molecules25010183. PMID: 31906391; PMCID: PMC6982783. 5: Gowri MS, Reaven GM, Azhar S. Effect of masoprocol on glucose transport and lipolysis by isolated rat adipocytes. Metabolism. 1999 Apr;48(4):411-4. doi: 10.1016/s0026-0495(99)90096-3. PMID: 10206430. 6: Luo J, Chuang T, Cheung J, Quan J, Tsai J, Sullivan C, Hector RF, Reed MJ, Meszaros K, King SR, Carlson TJ, Reaven GM. Masoprocol (nordihydroguaiaretic acid): a new antihyperglycemic agent isolated from the creosote bush (Larrea tridentata). Eur J Pharmacol. 1998 Apr 3;346(1):77-9. doi: 10.1016/s0014-2999(98)00139-3. PMID: 9617755. 7: Epstein E. Warning! Masoprocol is a potent sensitizer. J Am Acad Dermatol. 1994 Aug;31(2 Pt 1):295-7. doi: 10.1016/s0190-9622(08)81988-3. PMID: 8040425. 8: Filová E, Staňková L, Eckhardt A, Svobodová J, Musílková J, Pala J, Hadraba D, Brynda E, Koňařík M, Pirk J, Bačáková L. Modification of human pericardium by chemical crosslinking. Physiol Res. 2020 Feb 19;69(1):49-59. doi: 10.33549/physiolres.934335. Epub 2019 Dec 19. PMID: 31852209. 9: Daniels MJ, Nourse JB Jr, Kim H, Sainati V, Schiavina M, Murrali MG, Pan B, Ferrie JJ, Haney CM, Moons R, Gould NS, Natalello A, Grandori R, Sobott F, Petersson EJ, Rhoades E, Pierattelli R, Felli I, Uversky VN, Caldwell KA, Caldwell GA, Krol ES, Ischiropoulos H. Cyclized NDGA modifies dynamic α-synuclein monomers preventing aggregation and toxicity. Sci Rep. 2019 Feb 27;9(1):2937. doi: 10.1038/s41598-019-39480-z. PMID: 30814575; PMCID: PMC6393491. 10: Mundhe N, Kumar P, Arora I, Ahmed S, Lahkar M. Differential effect of NDGA on cisplatin-induced nephrotoxicity in Spargue-Dawley rats. Immunopharmacol Immunotoxicol. 2019 Feb;41(1):68-75. doi: 10.1080/08923973.2018.1547741. Epub 2019 Jan 3. PMID: 30604648.