WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H576892
CAS#: 180634-64-4 (pivalate)
Description: 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.
Hodoodo Cat#: H576892
Name: Masoprocol tetrapivalate
CAS#: 180634-64-4 (pivalate)
Chemical Formula: C38H54O8
Exact Mass: 638.38
Molecular Weight: 638.840
Elemental Analysis: C, 71.44; H, 8.52; O, 20.04
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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:
Biological target: | |
In vitro activity: | |
In vivo activity: |
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 |
Formulation protocol: | |
In vitro protocol: | |
In vivo protocol: |
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.