Nordihydroguaiaretic acid - CAS 500-38-9

Catalog:	BB026902
Product Name:	Nordihydroguaiaretic acid
CAS:	500-38-9
Synonyms:	4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol

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IUPAC Name:	4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol
Description:	NDGA (Nordihydroguaiaretic acid), also known as masoprocol, is a naturally occurring antioxidant dicatechol originally derived from the creosote bush Larrea divaricatta with antipromoter, anti-inflammatory, and antineoplastic activities. NDGA directly inhibits activation of two receptor tyrosine kinases (RTKs), the insulin-like growth factor receptor (IGF-1R) and the c-erbB2/HER2/neu receptor, resulting in decreased proliferation of susceptible tumor cell populations. This agent may induce apoptosis in susceptible tumor cell populations as a result of disruption of the actin cytoskeleton in association with the activation of stress activated protein kinases (SAPKs). In addition, NDGA inhibits arachidonic acid 5-lipoxygenase (5LOX), resulting in diminished synthesis of inflammatory mediators such as prostaglandins and leukotrines; it may prevent leukocyte infiltration into tissues and the release of reactive oxygen species and, at higher concentrations, may also inhibit cyclooxygenase.
Molecular Weight:	302.36
Molecular Formula:	C18H22O4
Canonical SMILES:	CC(CC1=CC(=C(C=C1)O)O)C(C)CC2=CC(=C(C=C2)O)O
InChI:	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
InChI Key:	HCZKYJDFEPMADG-UHFFFAOYSA-N
Boiling Point:	526.5 °C at 760 mmHg
Melting Point:	184-189°C
Flash Point:	247.8°C
Purity:	> 98 %
Density:	1.241 g/cm³
Solubility:	water, 4.969 mg/L @ 25 °C (est)
Appearance:	Powder
Storage:	Freezer (-20°C)
MDL:	MFCD00002206
LogP:	3.56640
Quality Standard:	Enterprise Standard
Refractive Index:	1.626
Stability:	Stable. Incompatible with oxidizing agents.

GHS Hazard Statement:	H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
Precautionary Statement:	P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501
Signal Word:	Warning

Publication Number	Title	Priority Date
US-11033516-B1	Combination therapies with disulfiram	20200918
US-11065214-B1	Combination therapies with disulfiram	20200918
EP-3838592-A1	Composition comprising polyesters for additive manufacturing	20191217
WO-2021122058-A1	Additive manufacturing process with a composition comprising polyesters	20191217
WO-2021076722-A1	Compositions and methods of treating acne and photoaging	20191016

PMID	Publication Date	Title	Journal
33352258	20210301	In vitro screening for chemical inhibition of the iodide recycling enzyme, iodotyrosine deiodinase	Toxicology in vitro : an international journal published in association with BIBRA
30561685	20190401	Screening the ToxCast Phase 1, Phase 2, and e1k Chemical Libraries for Inhibitors of Iodothyronine Deiodinases	Toxicological sciences : an official journal of the Society of Toxicology
29235845	20180119	Structure-Based Identification of HIV-1 Nucleocapsid Protein Inhibitors Active against Wild-Type and Drug-Resistant HIV-1 Strains	ACS chemical biology
28111842	20170701	Detoxification of benzo[a]pyrene primarily depends on cytochrome P450, while bioactivation involves additional oxidoreductases including 5-lipoxygenase, cyclooxygenase, and aldo-keto reductase in the liver	Journal of biochemical and molecular toxicology
25770929	20150525	Nordihydroguiaretic acid attenuates skin tumorigenesis in Swiss albino mice with the condition of topical co-administration of an immunosuppressant	Chemico-biological interactions

Complexity:	303
Compound Is Canonicalized:	Yes
Covalently-Bonded Unit Count:	1
Defined Atom Stereocenter Count:	0
Defined Bond Stereocenter Count:	0
Exact Mass:	302.15180918
Formal Charge:	0
Heavy Atom Count:	22
Hydrogen Bond Acceptor Count:	4
Hydrogen Bond Donor Count:	4
Isotope Atom Count:	0
Monoisotopic Mass:	302.15180918
Rotatable Bond Count:	5
Topological Polar Surface Area:	80.9 Å²
Undefined Atom Stereocenter Count:	2
Undefined Bond Stereocenter Count:	0
XLogP3:	4.3

Nordihydroguaiaretic acid - CAS 500-38-9

Technical Data

Safety and Hazards

Patents

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