nordihydroguaiaretic acid

1,4,4'-(2,3-dimethyl-1,4-butanediyl)bis-

CAS: 500-38-9 C18 H22 O4 MW: 302.37014000

Identification

Namenordihydroguaiaretic acid
CAS Number500-38-9
EINECS207-903-0
FDA UNIISearch
Molecular FormulaC18 H22 O4
Molecular Weight302.37014000
MDL NumberMFCD00002206
Nikkaji NumberJ9.195B
Beilstein2056826

Regulatory

JECFA Food AdditiveNordihydroguaiaretic Acid
FDA Mainterm (SATF)500-38-9 ; NORDIHYDROGUAIARETIC ACID--PROHIBITED
FDA RegulationFDA PART 175 -- INDIRECT FOOD ADDITIVES: ADHESIVES AND COMPONENTS OF COATINGS

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
Insoluble in water

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesantioxidants

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityoral-rat LD50 2000 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryfood contact resinous and polymeric coatings
Recommendation for nordihydroguaiaretic acid usage levels up tonot for fragrance use.
Recommendation for nordihydroguaiaretic acid flavor usage levels up tonot for flavor use.

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Potential Uses

antioxidants

Natural Occurrence

flax seed larrea divaricata

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 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.