8-formyl-1,6,7-trihydroxy-5-isopropyl-3-methyl-2,2'-bisnaphthalene

CAS: 303-45-7 C30 H30 O8 MW: 518.56270000

Identification

Namegossypol
IUPAC7-(8-formyl-1,6,7-trihydroxy-3-methyl-5-propan-2-ylnaphthalen-2-yl)-2,3,8-trihydroxy-6-methyl-4-propan-2-ylnaphthalene-1-carbaldehyde
CAS Number303-45-7
FDA UNIIKAV15B369O
Molecular FormulaC30 H30 O8
Molecular Weight518.56270000
MDL NumberMFCD00017352
Nikkaji NumberJ21.393D
Beilstein1917878

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 184.00 °C. @ 760.00 mm Hg
Boiling Point 707.89 °C. @ 760.00 mm Hg (est)
Flash Point 745.00 °F. TCC ( 395.90 °C. ) (est)
logP (o/w) 5.419 (est)
Soluble in water, 1.525e-005 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityoral-rat LD50 2315 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

Categorynatural substances and extractives
Recommendation for gossypol usage levels up tonot for fragrance use.
Recommendation for gossypol flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

cotton levant cotton seed cotton oil cotton seed okra seed soybean seed sunflower seed

Synonyms

(2,2'- binaphthalene)-8,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)- (2,2- binaphthalene)-8,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-, (±)- (2,2'- binaphthalene)-8,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl- [2,2'- binaphthalene]-8,8'-dicarboxaldehyde, 1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)- 7-(8- formyl-1,6,7-trihydroxy-3-methyl-5-(methylethyl)(2-naphthyl))-2,3,8-trihydroxy-6-methyl-4-(methylethyl)naphthalenecarbaldehyde 7-[8- formyl-1,6,7-trihydroxy-3-methyl-5-(methylethyl)(2-naphthyl)]-2,3,8-trihy droxy-6-methyl-4-(methylethyl)naphthalenecarbaldehyde 7-[8- formyl-1,6,7-trihydroxy-3-methyl-5-(methylethyl)(2-naphthyl)]-2,3,8-trihydroxy-6-methyl-4-(methylethyl)naphthalenecarbaldehyde 7-(8- formyl-1,6,7-trihydroxy-3-methyl-5-propan-2-ylnaphthalen-2-yl)-2,3,8-trihydroxy-6-methyl-4-propan-2-ylnaphthalene-1-carbaldehyde 8- formyl-1,6,7-trihydroxy-5-isopropyl-3-methyl-2,2'-bisnaphthalene 2,2'-bis(8- formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene) 2,2'-bis[8- formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene] (±)- gossypol racemic- gossypol gossypol, (±)-isomer 1,1',6,6',7,7'- hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-[2,2'-binaphthalene]-8,8'-dicarboxaldehyde 1,1',6,6',7,7'- hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-2,2'-binaphthalene-8,8'-dicarbaldehyde 1,1',6,6',7,7'- hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)[2,2'-binaphthalene]-8,8'-dicarboxaldehyde 1,1',6,6',7,7'- hexahydroxy-3,3'-dimethyl-5,5'-di(propan-2-yl)-2,2'-binaphthalene-8,8'-dicarbaldehyde 1,6,7,1',6',7'- hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-8,8'-dicarbaldehyde 1,1',6,6',7,7'- hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-2,2'-binaphthalene-8,8'-dicarbaldehyde 1,1',6,6',7,7'- hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl[2,2'-binaphthalene]-8,8'-dicarboxaldehyde 2,2'-bis(1,6,7- trihydroxy-3-methyl-5-isopropyl-8-aldehydonaphthalene) 2,2'-bis[1,6,7- trihydroxy-3-methyl-5-isopropyl-8-aldehydonaphthalene] PubMed: Comparative transcriptomic analysis of developing cotton cotyledons and embryo axis. PubMed: Effectiveness of albumin-conjugated gossypol as an immunogen to prevent gossypol-associated acute hepatotoxicity in rats. PubMed: (-)-Gossypol-enriched cottonseed oil inhibits proliferation and adipogenesis of human breast pre-adipocytes. PubMed: Effect of replacing soybean meal protein with protein from upland cottonseed, Pima cottonseed, or extruded Pima cottonseed on production of lactating dairy cows. PubMed: Impact of antinutritional factors in food proteins on the digestibility of protein and the bioavailability of amino acids and on protein quality. PubMed: Hemigossypol, a constituent in developing glanded cottonseed (Gossypium hirsutum). PubMed: Inhibitory effects of gossypol, gossypolone, and apogossypolone on a collection of economically important filamentous fungi. PubMed: Identification and proteomic analysis of a novel gossypol-degrading fungal strain. PubMed: Novel O-glycosidic gossypol isomers and their bioactivities. PubMed: Quercetin downregulates Mcl-1 by acting on mRNA stability and protein degradation. PubMed: Leptin and zeranol up-regulate cyclin D1 expression in primary cultured normal human breast pre-adipocytes. PubMed: Gossypol decreases tumor necrosis factor-α-induced intercellular adhesion molecule-1 expression via suppression of NF-κB activity. PubMed: Aromatase expression in leptin-pretreated human breast pre-adipocytes is enhanced by zeranol and suppressed by (-)-gossypol. PubMed: Responses of three successive generations of beet armyworm, Spodoptera exigua, fed exclusively on different levels of gossypol in cotton leaves. PubMed: Spermatotoxicity, biochemical changes and histological alteration induced by gossypol in testicular and hepatic tissues of male rats. PubMed: Gossypol--a polyphenolic compound from cotton plant. PubMed: Mutual anti-oxidative effect of gossypol acetic acid and gossypol-iron complex on hepatic lipid peroxidation in male rats. PubMed: Targeting of cancer energy metabolism. PubMed: Total and percent atropisomers of gossypol and gossypol-6-methyl ether in seeds from pima cottons and accessions of Gossypium barbadense L. PubMed: [Determination of gossypol in feeds by HPLC]. PubMed: Bioactivities of gossypol, 6-methoxygossypol, and 6,6'-dimethoxygossypol. PubMed: Preparation of an edible cottonseed protein concentrate and evaluation of its functional properties. PubMed: Engineering cottonseed for use in human nutrition by tissue-specific reduction of toxic gossypol. PubMed: Optimization of process parameters for reduction of gossypol levels in cottonseed meal by Candida tropicalis ZD-3 during solid substrate fermentation. PubMed: Isolation of 6-methoxy gossypol and 6,6'-dimethoxy gossypol from Gossypium barbadense Sea Island cotton. PubMed: Ratios of (+)- and (-)-gossypol in leaves, stems, and roots of selected accessions of Gossypium hirsutum var. marie galante (Watt) Hutchinson. PubMed: Gossypol toxicosis in a dog consequent to ingestion of cottonseed bedding. PubMed: Effects of source of gossypol and supplemental iron on plasma gossypol in Holstein steers. PubMed: Occurrence of (+)- and (-)-gossypol in wild species of cotton and in Gossypium hirsutum Var. marie-galante (Watt) Hutchinson. PubMed: Effects of antinutritional factors on protein digestibility and amino acid availability in foods. PubMed: Development of competitive direct ELISA for gossypol analysis. PubMed: [Determination of anti-nutrients in genetically modified crops]. PubMed: [Determination of free gossypol in meat by reversed-phased high performance liquid chromatography]. PubMed: Development of monoclonal antibody-based enzyme-linked immunosorbent assay for gossypol analysis in cottonseed meals. PubMed: Bollgard II cotton: compositional analysis and feeding studies of cottonseed from insect-protected cotton (Gossypium hirsutum L.) producing the Cry1Ac and Cry2Ab2 proteins. PubMed: Determination of gossypol enantiomer ratio in cotton plants by chiral higher-performance liquid chromatography. PubMed: Monoclonal antibodies for the analysis of gossypol in cottonseed products. PubMed: Irradiation effects on embryotoxicity and oxidative properties of gossypol dissolved in methanol. PubMed: Toxicity of (+)- and (-)-gossypol to the plant pathogen, Rhizoctonia solani. PubMed: Feeding cotton products to cattle. PubMed: Gossypol and gossypolone enantiomers in tissues of rainbow trout fed low and high levels of dietary cottonseed meal. PubMed: Effects of extrusion temperature and dwell time on aflatoxin levels in cottonseed. PubMed: Fermentation of cottonseed and other feedstuffs in cattle rumen fluid. PubMed: Antioxidative effects of cottonseed meals as evaluated in cooked meat. PubMed: Improved method for the rapid determination of terpenoid aldehydes in cotton. PubMed: Preference of female students for "tempe" preparations composed of glandless cottonseed and defatted soybean or corn at various ratios. PubMed: Effect of whole and expanded-expelled cottonseed on milk yield and blood gossypol. PubMed: Cottonseed with a high (+)- to (-)-gossypol enantiomer ratio favorable to broiler production. PubMed: Production, characterization, and application of anti-gossypol polyclonal antibodies. PubMed: Pathological lesions in lambs fed raw or processed cottonseed meal. PubMed: Environmental inhibition of 11beta-hydroxysteroid dehydrogenase. PubMed: Effect of coating whole cottonseed on performance of lactating dairy cows. PubMed: Response of lactating dairy cows to mechanically processed whole cottonseed. PubMed: The effect of nutrition on chemical toxicity. PubMed: Alteration of oxytocin-induced calcium oscillations in clone 9 cells by toxin exposure. PubMed: Infection with Trypanosoma brucei potentiates the antifertility effect of gossypol, especially in the protein-malnourished male rat. PubMed: Effects on dietary phosphorus of treating cottonseed meal with crystalline ferrous sulphate for the prevention of brown yolk discolouration. PubMed: Cottonseed protein: what does the future hold? PubMed: The effect of feeding whole cottonseed on the fertility of bulls. PubMed: Effects of free gossypol in the diet of pregnant and postpartum Brahman cows on calf development and cow performance. PubMed: In vitro rat pancreatic digestive enzyme activities and raw and heated glandless cottonseed and soybean flours. PubMed: Naturally occurring toxins in feedstuffs: Center for Veterinary Medicine Perspective. PubMed: Allelochemicals in plant foods and feedingstuffs: 1. Nutritional, biochemical and physiopathological aspects in animal production. PubMed: [Information on advances in sciences and technology. Advances in contraceptive technology]. PubMed: Protection by albumin against the pro-oxidant actions of phenolic dietary components. PubMed: A stoichiometric analysis of bovine serum albumin-gossypol interactions: a fluorescence quenching study. PubMed: A review of toxicity factors in some food and feedingstuffs in the nutrition of man and livestock in Nigeria. PubMed: Iron sulfate and feed pelleting to detoxify free gossypol in cottonseed diets for dairy cattle. PubMed: Effects of dietary cottonseed meal and iron-treated cottonseed meal in different laying hen genotypes. PubMed: Incidence and management of poisonings in livestock. PubMed: Effect of gossypol on thyroid hormones in young female rats. PubMed: Gossypol residues in organ meats vs thresholds of toxicity. PubMed: Effects of dietary cottonseed meal, with and without iron treatment, on laying hens. PubMed: Gossypol as a toxicant in livestock. PubMed: Failure of oral gossypol to inhibit hepatic microsomal and cytosolic drug-metabolising enzymes. PubMed: The future of male birth control. PubMed: Worldwide trends in funding for contraceptive research and evaluation. PubMed: Spectrophotometric determination of total gossypol in cottonseeds and cottonseed meals. PubMed: Looking into the future. PubMed: Detoxification and nutritional evaluation of solvent extracted Egyptian cottonseed meal. PubMed: Gossypol in cottonseed products: toxicology and inactivation. PubMed: Gossypol: a possible male antifertility agent. Report of a workshop. PubMed: Sounding board. The politics of contraception: the view from Beijing. PubMed: Two food applications of cottonseed flours and meals. PubMed: Potential for improving cottonseed quality by genetic and agronomic practices. PubMed: Cottonseed protein derivatives as nutritional and functional supplements in food formulations. PubMed: Effect of processing on protein utilization by ruminants. PubMed: [Utilization of gossypol-free cottonseed and its by-products as human food]. PubMed: A comparison of chemical methods for the determination of available lysine in various proteins. PubMed: Protein products and hulls for animal foods. PubMed: Fish meal supplementation of chick starting rations containing cottonseed cake. PubMed: Cottonseed colour fixed pigments. Part II. Role of hexane isomers on oil quality. PubMed: Effect of free and bound gossypol on the absorption of L-]14-C]lysine, L-[14-C]methionine, and L-[14-C]valine from the rat small intestine. PubMed: Effect of free gossypol on tissue uptake of iron by everted segments of rat duodenum. PubMed: Preparation of low-gossypol cottonseed flour. PubMed: Hematological effects of injected gossypol and iron in rats. PubMed: [Extraction and precipitation of cottonseed protein by the wet method]. PubMed: Fungal-treated cottonseed meal for swine. PubMed: Natural non-nutrient substances in the food chain. PubMed: Effect of gossypol bound to cottonseed protein on growth of weanling rats. PubMed: [Method of wet concentration of protein of cotton seed cake processed by screw press]. PubMed: Energy value of cottonseed meal for swine. PubMed: Cottonseed meal, dehydrated grass and ascorbic acid as dietary factors preventing toxicity of vanadium for the chick. PubMed: Lipid composition of vegetable oils. PubMed: Effects of dietary iron on gossypol accumulation in and elimination from porcine liver. PubMed: The in vivo effect of gossypol on cytochrome oxidase, succinoxidase, and succinic dehydrogenase in animal tissues. PubMed: Effect of single and repeated doses of gossypol on the rat.