nordihydroguaiaretic acid
1,4,4'-(2,3-dimethyl-1,4-butanediyl)bis-
 
Notes:
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. Antioxidant. Formerly approved as a food additive; now banned by FDA (USA) Masoprocol is a novel antineoplastic agent. It is not known exactly how masoprocol works. Laboratory experiments have shown that masoprocol prevents cells similar to the ones found in actinic keratoses from multiplying. Masoprocol was withdrawn from the U.S. market in June 1996.
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4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol (Click)
CAS Number: 500-38-9Picture of molecule
ECHA EINECS - REACH Pre-Reg: 207-903-0
Nikkaji Web: J9.195B
Beilstein Number: 2056826
MDL: MFCD00002206
XlogP3-AA: 4.30 (est)
Molecular Weight: 302.37014000
Formula: C18 H22 O4
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: food contact resinous and polymeric coatings
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
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IBM Patents: Obtain
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PubMed: Search
NCBI: Search
JECFA Food Additive: Nordihydroguaiaretic Acid
FDA Mainterm: NORDIHYDROGUAIARETIC ACID--PROHIBITED
FDA Regulation:
FDA PART 175 -- INDIRECT FOOD ADDITIVES: ADHESIVES AND COMPONENTS OF COATINGS
Subpart C--Substances for Use as Components of Coatings
Sec. 175.300 Resinous and polymeric coatings.


FDA PART 177 -- INDIRECT FOOD ADDITIVES: POLYMERS
Subpart B--Substances for Use as Basic Components of Single and Repeated Use Food Contact
Sec. 177.1010 Acrylic and modified acrylic plastics, semirigid and rigid.


FDA PART 181 -- PRIOR-SANCTIONED FOOD INGREDIENTS
Subpart B--Specific Prior-Sanctioned Food Ingredients
Sec. 181.24 Antioxidants.


FDA PART 189 -- SUBSTANCES PROHIBITED FROM USE IN HUMAN FOOD
Subpart C--Substances Generally Prohibited From Direct Addition or Use as Human Food
Sec. 189.165 Nordihydroguaiaretic acid (NDGA).
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Physical Properties:
Appearance: white to gray crystalline solid (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Melting Point: 185.00 to  186.00 °C. @ 0.00 mm Hg
logP (o/w): 4.640 (est)
Soluble in:
 alcohol
 ether
 propylene glycol
 water, 4.969 mg/L @ 25 °C (est)
Insoluble in:
 water
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Organoleptic Properties:
  
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: antioxidants
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Suppliers:
EMD Millipore
For experimental / research use only.
NDGA
ExtraSynthese
For experimental / research use only.
norDihydroguaiaretic Acid
Santa Cruz Biotechnology
For experimental / research use only.
NDGA (Nordihydroguaiaretic acid) ≥95%
Sigma-Aldrich: Aldrich
For experimental / research use only.
norDihydroguaiaretic Acid ≥97.0% (HPLC)
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50  2000 mg/kg
Journal of the American Oil Chemists' Society. Vol. 54, Pg. 239, 1977.

oral-mouse LD50  2000 mg/kg
Journal of the American Oil Chemists' Society. Vol. 54, Pg. 239, 1977.

intraperitoneal-mouse LD50  550 mg/kg
Advances in Food Research. Vol. 3, Pg. 197, 1951.

oral-guinea pig LD50  830 mg/kg
Advances in Food Research. Vol. 3, Pg. 197, 1951.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: food contact resinous and polymeric coatings
Recommendation for nordihydroguaiaretic acid usage levels up to:
 not for fragrance use.
 
Recommendation for nordihydroguaiaretic acid flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
ClinicalTrials.gov: search
Chemical Carcinogenesis Research Information System: Search
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
Env. Mutagen Info. Center: Search
NLM Developmental and Reproductive Toxicity: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 4534
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol
Chemidplus: 0000500389
RTECS: UX1750000 for cas# 500-38-9
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References:
 4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 4534
Pubchem (sid): 134977974
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
FDA Everything Added to Food in the United States (EAFUS): View
CHEBI: View
CHEMBL: View
KEGG (GenomeNet): C10719
HMDB (The Human Metabolome Database): HMDB12270
FooDB: FDB011903
Export Tariff Code: 2907.29.6000
VCF-Online: VCF Volatile Compounds in Food
Wikipedia: View
RSC Learn Chemistry: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
 antioxidants 
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Occurrence (nature, food, other): note
 flax seed
Search Trop  Picture
 larrea divaricata
Search Trop  Picture
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Synonyms:
1,2-benzenediol, 4,4'-(2,3-dimethyl-1,4-butanediyl)bis-
 butane, 1,4-bis(3,4-dihydroxyphenyl)-2,3-dimethyl-
2,3-bis(3,4-dihydroxybenzyl)butane
2,3-bis(3,4-dihydroxyphenyl methyl) butane
1,4-bis(3,4-dihydroxyphenyl)-2,3-dimethylbutane
4-[4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol
2,3-bis(3,4-dihydroxyphenylmethyl)butane
4,4'-(2,3-dimethyl tetramethylene) dipyrocatechol
2,3-dimethyl-1,4-bis(3,4-dihydroxyphenyl)butane
1,4,4'-(2,3-dimethyl-1,4-butanediyl)bis-
4,4'-(2,3-dimethyl-1,4-butanediyl)bis-1,2-benzenediol
4,4'-(2,3-dimethyl-1,4-butanediyl)bis(1,2-benzenediol)
4,3-dimethyl-1,4-butanediyl)bis(pyrocatechol)
4,4'-(2,3-dimethyl-1,4-butanediyl)bis(pyrocatechol)
4,4'-[2,3-dimethyl-1,4-butanediyl]-bis[1,2-benzenediol
4,3-dimethyltetramethylene)dipyrocatechol
4,4'-(2,3-dimethyltetramethylene)dipyrocatechol
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Articles:
PubMed: Metmyoglobin reduction by polyphenols and mechanism of the conversion of metmyoglobin to oxymyoglobin by quercetin.
PubMed: Anticholinesterase activity of phenolic acids and their derivatives.
PubMed: Ovariectomized mouse uterotrophic assay of 36 chemicals.
PubMed: Structure and function of the oxidation products of polyphenols and identification of potent lipoxygenase inhibitors from Fe-catalyzed oxidation of resveratrol.
PubMed: Argentinean Andean propolis associated with the medicinal plant Larrea nitida Cav. (Zygophyllaceae). HPLC-MS and GC-MS characterization and antifungal activity.
PubMed: Inhibition of rat mammary microsomal oxidation of ethanol to acetaldehyde by plant polyphenols.
PubMed: In vitro growth-inhibitory effect of plant-derived extracts and compounds against Paenibacillus larvae and their acute oral toxicity to adult honey bees.
PubMed: Jasmonic acid is induced in a biphasic manner in response of pea seedlings to wounding.
PubMed: Single-laboratory validated method for determination of nordihydroguaiaretic acid in chaparral-containing dietary supplements.
PubMed: Nordihydroguaiaretic acid attenuates potassium dichromate-induced oxidative stress and nephrotoxicity.
PubMed: Monensin causes transient calcium ion influx into mouse splenic lymphocytes in a sodium ion-independent fashion.
PubMed: Baicalein induction of hydroxyl radical formation via 12-lipoxygenase in human platelets: an ESR study.
PubMed: Prooxidant activity and toxicity of nordihydroguaiaretic acid in clone-9 rat hepatocyte cultures.
PubMed: Inhibition of 12- and 15-lipoxygenase activities and protection of human and tilapia low density lipoprotein oxidation by I-Tiao-Gung (Glycine tomentella).
PubMed: Conjugated linoleic acid, cis-9,trans-11, is a substrate for pulmonary 15-lipoxygenase-1 in rat.
PubMed: Determination and confirmation of five phenolic antioxidants in foods by LC/MS and GC/MS.
PubMed: Larrea tridentata (Creosote bush), an abundant plant of Mexican and US-American deserts and its metabolite nordihydroguaiaretic acid.
PubMed: Oxidant-stimulated chloride secretion in rat jejunum in vitro is mediated by eicosanoids.
PubMed: [Simultaneous determination of five antioxidants in food by HPLC with fluorescence detection].
PubMed: Lipoxygenase inhibitors inhibit heparin-releasable lipoprotein lipase activity in 3T3-L1 adipocytes and enhance body fat reduction in mice by conjugated linoleic acid.
PubMed: trans-10,cis-12-Conjugated linoleic acid reduces leptin secretion from 3T3-L1 adipocytes.
PubMed: Effect of a restricted diet on the metabolism of glucose in uteri isolated from immature rats: influence of indomethacin and nordihydroguaiaretic acid.
PubMed: Stimulation of the stress-induced expression of stress proteins by curcumin in cultured cells and in rat tissues in vivo.
PubMed: Lipoxygenase-1 from soybean seed inhibiting the activity of pancreatic lipase.
PubMed: Proliferative responses of normal human mammary and MCF-7 breast cancer cells to linoleic acid, conjugated linoleic acid and eicosanoid synthesis inhibitors in culture.
PubMed: Characterization of the pattern of inflammatory cell influx in chicks following the intraperitoneal administration of live Salmonella enteritidis and Salmonella enteritidis-immune lymphokines.
PubMed: Suppression of hydroperoxide-induced cytotoxicity by polyphenols.
PubMed: Characteristics and specificity of the inhibition of liver glucose-6-phosphatase by arachidonic acid. Lesser inhibitability of the enzyme of diabetic rats.
PubMed: Suppression of hydrogen peroxide-induced mammalian cytotoxicity by nordihydroguaiaretic acid.
PubMed: Effect of chronic underfeeding on uterine glycogen of rats. Influence of indomethacin and nordihydroguaiaretic acid.
PubMed: Comparison of the cytotoxicity of different hydroperoxides to V79 cells.
PubMed: Compound interactions effects of plant antioxidants in combination with carbaryl on performance ofTrichoplusia ni (Cabbage Looper).
PubMed: Inhibition of 12-O-tetradecanoylphorbol-13-acetate-enhanced transformation in vitro by inhibitors of phospholipid metabolism.
PubMed: Oxidant-induced haemoprotein degradation in rat tissue slices: effect of bromotrichloromethane, antioxidants and chelators.
PubMed: Liquid chromatographic determination of seven antioxidants in dry food.
PubMed: Arachidonic acid metabolism of cultured peritoneal rat macrophages and its manipulation by nonsteroidal antiinflammatory agents.
PubMed: Initiation of lipid peroxidation in biological systems.
PubMed: High performance liquid chromatographic determination of seven antioxidants in oil and lard: collaborative study.
PubMed: Effects of antioxidants on lipid peroxide formation in irradiated synthetic diets.
PubMed: Liquid chromatography with amperometric detection for determinging phenolic preservatives.
PubMed: High performance liquid chromatographic determination of nine phenolic antioxidants in oils, lards, and shortenings.
PubMed: A rapid gas-liquid chromatographic method for the multi-determination of antioxidants in fats, oils and dried food products.
PubMed: A cystic nephropathy induced by nordihydroguaiaretic acid in the rat. Light and electron microscopic investigations.
PubMed: Toxic properties of nordihydroguaiaretic acid.
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