Masoprocol

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

MedKoo CAT#: 412860

CAS#: 27686-84-6 (RS-isomer)

Description: 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

img
Masoprocol
CAS# 27686-84-6 (RS-isomer)
Instruction

Theoretical Analysis

MedKoo Cat#: 412860
Name: Masoprocol
CAS#: 27686-84-6 (RS-isomer)
Chemical Formula: C18H22O4
Exact Mass: 302.15
Molecular Weight: 302.370
Elemental Analysis: C, 71.50; H, 7.33; O, 21.16

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.

Request quote for custom synthesis

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

Synonym: Masoprocol; CHX100; CHX-100; CHX 100; nordihydroguaiaretic acid, NDGA, and actine;

IUPAC/Chemical Name: 4,4'-((2R,3S)-2,3-dimethylbutane-1,4-diyl)bis(benzene-1,2-diol)

InChi Key: HCZKYJDFEPMADG-TXEJJXNPSA-N

InChi Code: InChI=1S/C18H22O4/c1-11(7-13-3-5-15(19)17(21)9-13)12(2)8-14-4-6-16(20)18(22)10-14/h3-6,9-12,19-22H,7-8H2,1-2H3/t11-,12+

SMILES Code: C[C@@H]([C@H](Cc1cc(O)c(O)cc1)C)Cc2cc(O)c(O)cc2

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 302.37 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:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

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.