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Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00
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| Food Chemicals Codex Listed: | No |
| Soluble in: |
| | water, 169.9 mg/L @ 25 °C (est) |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
Safety Information:
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| Hazards identification |
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| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
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| Pictogram | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
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Not determined
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | | natural substances and extractives |
| Recommendation for O-desmethylangolensin usage levels up to: | | | not for fragrance use.
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| |
| Recommendation for O-desmethylangolensin flavor usage levels up to: |
| | not for flavor use.
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Safety References:
European Food Safety Authority (EFSA) reference(s):
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Risk assessment for peri- and post-menopausal women taking food supplements containing isolated isoflavones
View page or View pdf
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| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :89472 |
| National Institute of Allergy and Infectious Diseases:Data |
| 1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)propan-1-one |
| Chemidplus:0021255696 |
| RTECS:TJ7525000 for cas# 21255-69-6 |
References:
| | 1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)propan-1-one |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 89472 |
| Pubchem (sid): | 135045450 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| 1-(2,4- | dihydroxyphenyl)-2-(4-hydroxyphenyl)propan-1-one | | 1- | propanone, 1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)- |
Articles:
| PubMed:Urinary isoflavonoids and risk of type 2 diabetes: a prospective investigation in US women. |
| PubMed:Isoflavone Pharmacokinetics and Metabolism after Consumption of a Standardized Soy and Soy-Almond Bread in Men with Asymptomatic Prostate Cancer. |
| PubMed:Red clover isoflavone metabolite bioavailability is decreased after fructooligosaccharide supplementation. |
| PubMed:Urinary enterolactone associated with liver enzyme levels in US adults: National Health and Nutrition Examination Survey (NHANES). |
| PubMed:Urinary enterolactone is associated with obesity and metabolic alteration in men in the US National Health and Nutrition Examination Survey 2001-10. |
| PubMed:Urinary phytoestrogens in relation to metabolic disturbances among children and adolescents. |
| PubMed:Enhanced biosynthesis of O-desmethylangolensin from daidzein by a novel oxygen-tolerant cock intestinal bacterium in the presence of atmospheric oxygen. |
| PubMed:Soy provides modest benefits on endothelial function without affecting inflammatory biomarkers in adults at cardiometabolic risk. |
| PubMed:Stereochemical determination of O-desmethylangolensin produced from daidzein. |
| PubMed:Fecal bacterial community changes associated with isoflavone metabolites in postmenopausal women after soy bar consumption. |
| PubMed:Obesity prevalence in relation to gut microbial environments capable of producing equol or O-desmethylangolensin from the isoflavone daidzein. |
| PubMed:R(-)-O-desmethylangolensin is the main enantiomeric form of daidzein metabolite produced by human in vitro and in vivo. |
| PubMed:Cardiovascular risks in relation to daidzein metabolizing phenotypes among Chinese postmenopausal women. |
| PubMed:Chiroptical study and absolute configuration of (-)-O-DMA produced from daidzein metabolism. |
| PubMed:Feeding soybean meal increases the blood level of isoflavones and reduces the steroidogenic capacity in bovine corpora lutea, without affecting peripheral progesterone concentrations. |
| PubMed:Urinary isoflavone concentrations are inversely associated with cardiometabolic risk markers in pregnant U.S. women. |
| PubMed:Urinary phytoestrogen levels and frailty in older American women of the National Health and Nutrition Examination Survey (NHANES) 1999-2002: a cross-sectional study. |
| PubMed:O-desmethylangolensin inhibits the proliferation of human breast cancer MCF-7 cells by inducing apoptosis and promoting cell cycle arrest. |
| PubMed:The antioxidant activity of daidzein metabolites, O‑desmethylangolensin and equol, in HepG2 cells. |
| PubMed:Isoflavone metabolism and bone-sparing effects of daidzein-metabolites. |
| PubMed:Sociodemographic and lifestyle variables are compound- and class-specific correlates of urine phytoestrogen concentrations in the U.S. population. |
| PubMed:Associations between urinary soy isoflavonoids and two inflammatory markers in adults in the United States in 2005-2008. |
| PubMed:Anticancer effects of O-desmethylangolensin are mediated through cell cycle arrest at the G2/M phase and mitochondrial-dependent apoptosis in Hep3B human hepatocellular carcinoma cells. |
| PubMed:Isoflavone metabolism in domestic cats (Felis catus): comparison of plasma metabolites detected after ingestion of two different dietary forms of genistein and daidzein. |
| PubMed:Effect of the genistein metabolite on leptin secretion in murine adipocytes in vitro. |
| PubMed:Urinary isoflavonoids and risk of coronary heart disease. |
| PubMed:Daidzein-metabolizing phenotypes in relation to bone density and body composition among premenopausal women in the United States. |
| PubMed:Correlations of urinary phytoestrogen excretion with lifestyle factors and dietary intakes among middle-aged and elderly Chinese women. |
| PubMed:O-desmethylangolensin: the importance of equol's lesser known cousin to human health. |
| PubMed:Dietary isoflavone absorption, excretion, and metabolism in captive cheetahs (Acinonyx jubatus). |
| PubMed:Phytoestrogen biomonitoring: an extractionless LC-MS/MS method for measuring urinary isoflavones and lignans by use of atmospheric pressure photoionization (APPI). |
| PubMed:Complete genomic sequence of the O-desmethylangolensin-producing bacterium Clostridium rRNA cluster XIVa strain SY8519, isolated from adult human intestine. |
| PubMed:Dairy consumption is a significant correlate of urinary equol concentration in a representative sample of US adults. |
| PubMed:[Research development on relation between equol and soy foods health effect]. |
| PubMed:Improved in vitro assays of superoxide anion and 1,1-diphenyl- 2-picrylhydrazyl (DPPH) radical-scavenging activity of isoflavones and isoflavone metabolites. |
| PubMed:Deglycosylation of puerarin and other aromatic C-glucosides by a newly isolated human intestinal bacterium. |
| PubMed:Urinary metabolites as biomarkers of polyphenol intake in humans: a systematic review. |
| PubMed:Profiles of phytoestrogens in human urine from several Asian countries. |
| PubMed:Urine accurately reflects circulating isoflavonoids and ascertains compliance during soy intervention. |
| PubMed:Overnight urinary excretion of isoflavones as an indicator for dietary isoflavone intake in Korean girls of pubertal age. |
| PubMed:Development of a high-throughput LC/APCI-MS method for the determination of thirteen phytoestrogens including gut microbial metabolites in human urine and serum. |
| PubMed:Daidzein-metabolising phenotypes in relation to serum lipids and uric acid in adults in Guangzhou, China. |
| PubMed:The red clover isoflavone irilone is largely resistant to degradation by the human gut microbiota. |
| PubMed:Characterization of an O-desmethylangolensin-producing bacterium isolated from human feces. |
| PubMed:[C-ring cleavage of isoflavone daidzein by a newly-isolated facultative Enterococcus hirae AUH-HM195 from Crossoptilon mantchuricum feces]. |
| PubMed:Is equol the key to the efficacy of soy foods? |
| PubMed:Dietary seaweed modifies estrogen and phytoestrogen metabolism in healthy postmenopausal women. |
| PubMed:Comparative study on the nuclear hormone receptor activity of various phytochemicals and their metabolites by reporter gene assays using Chinese hamster ovary cells. |
| PubMed:The role of diet in the metabolism of daidzein by human faecal microbiota sampled from Italian volunteers. |
| PubMed:Phytoestrogens and phytoestrogen metabolites differentially modulate immune parameters in human leukocytes. |
| PubMed:Lack of prospective associations between plasma and urinary phytoestrogens and risk of prostate or colorectal cancer in the European Prospective into Cancer-Norfolk study. |
| PubMed:Gastrointestinal absorption and metabolism of soy isoflavonoids in ileal-canulated swine. |
| PubMed:Daidzein-metabolizing phenotypes in relation to mammographic breast density among premenopausal women in the United States. |
| PubMed:Receptor binding and transactivation activities of red clover isoflavones and their metabolites. |
| PubMed:Urinary isoflavones are increased in adults, but decreased in children, consuming soy when on oral antibiotic therapy. |
| PubMed:Red clover extract: a putative source for simultaneous treatment of menopausal disorders and the metabolic syndrome. |
| PubMed:Comparative activities of daidzein metabolites, equol and O-desmethylangolensin, on bone mineral density and lipid metabolism in ovariectomized mice and in osteoclast cell cultures. |
| PubMed:Daidzein-metabolizing phenotypes in relation to serum hormones and sex hormone binding globulin, and urinary estrogen metabolites in premenopausal women in the United States. |
| PubMed:Oral antibiotics decrease urinary isoflavonoid excretion in children after soy consumption. |
| PubMed:Breast cancer risk in relation to urinary and serum biomarkers of phytoestrogen exposure in the European Prospective into Cancer-Norfolk cohort study. |
| PubMed:Demographic, anthropometric, and lifestyle factors and dietary intakes in relation to daidzein-metabolizing phenotypes among premenopausal women in the United States. |
| PubMed:Determination of urinary phytoestrogens by HPLC-MS/MS: a comparison of atmospheric pressure chemical ionization (APCI) and electrospray ionization (ESI). |
| PubMed:Phytoestrogen exposure is associated with circulating sex hormone levels in postmenopausal women and interact with ESR1 and NR1I2 gene variants. |
| PubMed:Metabolism of isoflavones, lignans and prenylflavonoids by intestinal bacteria: producer phenotyping and relation with intestinal community. |
| PubMed:Quantitative determination of acetyl glucoside isoflavones and their metabolites in human urine using combined liquid chromatography-mass spectrometry. |
| PubMed:Variations in plasma phytoestrogen concentrations in European adults. |
| PubMed:Isoflavonoid glucosides are deconjugated and absorbed in the small intestine of human subjects with ileostomies. |
| PubMed:High throughput quantification of phytoestrogens in human urine and serum using liquid chromatography/tandem mass spectrometry (LC-MS/MS). |
| PubMed:Assessment of dietary isoflavone intake among middle-aged Chinese men. |
| PubMed:Plasma phytoestrogens and subsequent breast cancer risk. |
| PubMed:Phytoestrogen exposure, polymorphisms in COMT, CYP19, ESR1, and SHBG genes, and their associations with prostate cancer risk. |
| PubMed:Consumption of Lactobacillus acidophilus and Bifidobacterium longum does not alter phytoestrogen metabolism and plasma hormones in men: a pilot study. |
| PubMed:Production of equol from daidzein by gram-positive rod-shaped bacterium isolated from rat intestine. |
| PubMed:Isoflavone metabolites and their in vitro dual functions: they can act as an estrogenic agonist or antagonist depending on the estrogen concentration. |
| PubMed:Lignan and isoflavone excretion in relation to uterine fibroids: a case-control study of young to middle-aged women in the United States. |
| PubMed:Reduced isoflavone metabolites formed by the human gut microflora suppress growth but do not affect DNA integrity of human prostate cancer cells. |
| PubMed:Prevalence of daidzein-metabolizing phenotypes differs between Caucasian and Korean American women and girls. |
| PubMed:Prostatic fluid concentrations of isoflavonoids in soy consumers are sufficient to inhibit growth of benign and malignant prostatic epithelial cells in vitro. |
| PubMed:High concordance of daidzein-metabolizing phenotypes in individuals measured 1 to 3 years apart. |
| PubMed:Characterization and quantification of soy isoflavone metabolites in serum of renal transplanted patients by high-performance liquid chromatography/electrospray ionization mass spectrometry. |
| PubMed:Polymorphisms in the CYP19 gene may affect the positive correlations between serum and urine phytoestrogen metabolites and plasma androgen concentrations in men. |
| PubMed:Metabolism of glycitein (7,4'-dihydroxy-6-methoxy-isoflavone) by human gut microflora. |
| PubMed:Postmenopausal bone mineral density in relation to soy isoflavone-metabolizing phenotypes. |
| PubMed:Long-term dietary habits affect soy isoflavone metabolism and accumulation in prostatic fluid in caucasian men. |
| PubMed:Urinary phytoestrogen concentrations in the U.S. population (1999-2000). |
| PubMed:Optimization of conditions for the enzymatic hydrolysis of phytoestrogen conjugates in urine and plasma. |
| PubMed:Gut bacterial metabolism of the soy isoflavone daidzein: exploring the relevance to human health. |
| PubMed:Automated online and off-line solid-phase extraction methods for measuring isoflavones and lignans in urine. |
| PubMed:Phytoestrogen exposure correlation with plasma estradiol in postmenopausal women in European Prospective Investigation of Cancer and Nutrition-Norfolk may involve diet-gene interactions. |
| PubMed:Isolation and characterisation of an equol-producing mixed microbial culture from a human faecal sample and its activity under gastrointestinal conditions. |
| PubMed:Reports: plasma and dietary phytoestrogens and risk of premalignant lesions of the cervix. |
| PubMed:Familial correlations, segregation analysis, and nongenetic correlates of soy isoflavone-metabolizing phenotypes. |
| PubMed:Influence of 10 wk of soy consumption on plasma concentrations and excretion of isoflavonoids and on gut microflora metabolism in healthy adults. |
| PubMed:Mammographic density in relation to daidzein-metabolizing phenotypes in overweight, postmenopausal women. |
| PubMed:Phytoestrogen concentrations in serum and spot urine as biomarkers for dietary phytoestrogen intake and their relation to breast cancer risk in European prospective investigation of cancer and nutrition-norfolk. |
| PubMed:Serum steroid hormones, sex hormone-binding globulin concentrations, and urinary hydroxylated estrogen metabolites in post-menopausal women in relation to daidzein-metabolizing phenotypes. |
| PubMed:Studies of the in vitro intestinal metabolism of isoflavones aid in the identification of their urinary metabolites. |
| PubMed:Differential effects of isoflavones and lignans on invasiveness of MDA-MB-231 breast cancer cells in vitro. |
| PubMed:Influence of soya-based infant formula consumption on isoflavone and gut microflora metabolite concentrations in urine and on faecal microflora composition and metabolic activity in infants and children. |
| PubMed:In vitro incubation of human feces with daidzein and antibiotics suggests interindividual differences in the bacteria responsible for equol production. |
| PubMed:Interactions of phytoestrogens with estrogen receptors alpha and beta (III). Estrogenic activities of soy isoflavone aglycones and their metabolites isolated from human urine. |
| PubMed:Genotoxic activity of four metabolites of the soy isoflavone daidzein. |
| PubMed:Urinary equol excretion in relation to 2-hydroxyestrone and 16alpha-hydroxyestrone concentrations: an observational study of young to middle-aged women. |
| PubMed:Serum isoflavones and soya food intake in Japanese, Thai and American end-stage renal disease patients on chronic haemodialysis. |
| PubMed:Urinary and serum concentrations of seven phytoestrogens in a human reference population subset. |
| PubMed:Quantification of isoflavones and lignans in serum using isotope dilution liquid chromatography/tandem mass spectrometry. |
| PubMed:Variations in metabolism of the soy isoflavonoid daidzein by human intestinal microfloras from different individuals. |
| PubMed:Transformation of flavonoids by intestinal microorganisms. |
| PubMed:Bioavailability of phyto-oestrogens. |
| PubMed:Quantification of isoflavones and lignans in urine using gas chromatography/mass spectrometry. |
| PubMed:Metabolism of isoflavones and lignans by the gut microflora: a study in germ-free and human flora associated rats. |
| PubMed:Isoflavonoid and lignan phytoestrogens as dietary biomarkers. |
| PubMed:Time-resolved fluoroimmunoassay of plasma and urine O-desmethylangolensin. |
| PubMed:Liquid chromatographic-photodiode array mass spectrometric analysis of dietary phytoestrogens from human urine and blood. |
| PubMed:Hydrolysis of isoflavone glycosides to aglycones by beta-glycosidase does not alter plasma and urine isoflavone pharmacokinetics in postmenopausal women. |
| PubMed:Anaerobic C-ring cleavage of genistein and daidzein by Eubacterium ramulus. |
| PubMed:Characterization of isoflavones and their conjugates in female rat urine using LC/MS/MS. |
| PubMed:Overnight urinary isoflavone excretion in a population of women living in the United States, and its relationship to isoflavone intake. |
| PubMed:Comparative metabolism of genistin by human and rat gut microflora: detection and identification of the end-products of metabolism. |
| PubMed:Assaying the estrogenicity of phytoestrogens in cells of different estrogen sensitive tissues. |
| PubMed:Disposition and biotransformation of the estrogenic isoflavone daidzein in rats. |
| PubMed:Comparison of isoflavones among dietary intake, plasma concentration and urinary excretion for accurate estimation of phytoestrogen intake. |
| PubMed:Urinary isoflavonoid and lignan excretion on a Western diet: relation to soy, vegetable, and fruit intake. |
| PubMed:Biotransformation of genistein in the rat: elucidation of metabolite structure by product ion mass fragmentology. |
| PubMed:Identification of isoflavone metabolites dihydrodaidzein, dihydrogenistein, 6'-OH-O-dma, and cis-4-OH-equol in human urine by gas chromatography-mass spectroscopy using authentic reference compounds. |
| PubMed:Sensitive high-performance liquid chromatographic method for profiling phytoestrogens using coulometric electrode array detection: application to plasma analysis. |
| PubMed:Usual dietary consumption of soy foods and its correlation with the excretion rate of isoflavonoids in overnight urine samples among Chinese women in Shanghai. |
| PubMed:Urinary excretion of isoflavonoids and the risk of breast cancer. |
| PubMed:Isoflavones in human breast milk and other biological fluids. |
| PubMed:Reliability of serum measurements of lignans and isoflavonoid phytoestrogens over a two-year period. |
| PubMed:Pharmacokinetics of soybean isoflavones in plasma, urine and feces of men after ingestion of 60 g baked soybean powder (kinako). |
| PubMed:Inhibitory effects of soy and rye diets on the development of Dunning R3327 prostate adenocarcinoma in rats. |
| PubMed:Urinary equol excretion with a soy challenge: influence of habitual diet. |
| PubMed:HPLC analysis of isoflavonoids and other phenolic agents from foods and from human fluids. |
| PubMed:Isoflavonoid levels in spot urine are associated with frequency of dietary soy intake in a population-based sample of middle-aged and older Chinese in Singapore. |
| PubMed:Urinary isoflavonoid excretion in humans is dose dependent at low to moderate levels of soy-protein consumption. |
| PubMed:Daidzein and genistein concentrations in human milk after soy consumption. |
| PubMed:Analysis of plasma isoflavones by reversed-phase HPLC-multiple reaction ion monitoring-mass spectrometry. |
| PubMed:Vegetables, fruits, and legumes: effect on urinary isoflavonoid phytoestrogen and lignan excretion. |
| PubMed:Urinary isoflavonoid phytoestrogen and lignan excretion after consumption of fermented and unfermented soy products. |
| PubMed:Isotope dilution gas chromatographic-mass spectrometric method for the determination of unconjugated lignans and isoflavonoids in human feces, with preliminary results in omnivorous and vegetarian women. |
| PubMed:The variable metabolic response to dietary isoflavones in humans. |
| PubMed:Lignan and isoflavonoid conjugates in human urine. |
| PubMed:Urinary lignan and isoflavonoid excretion in men and women consuming vegetable and soy diets. |
| PubMed:High-performance liquid chromatographic assay of isoflavonoids and coumestrol from human urine. |
| PubMed:Urinary lignan and isoflavonoid excretion in premenopausal women consuming flaxseed powder. |
| PubMed:Metabolites of dietary (soya) isoflavones in human urine. |
| PubMed:Plasma concentrations of phyto-oestrogens in Japanese men. |
| PubMed:Quantitative determination of lignans and isoflavonoids in plasma of omnivorous and vegetarian women by isotope dilution gas chromatography-mass spectrometry. |
| PubMed:Urinary excretion of lignans and isoflavonoid phytoestrogens in Japanese men and women consuming a traditional Japanese diet. |
| PubMed:Isotope dilution gas chromatographic-mass spectrometric method for the determination of lignans and isoflavonoids in human urine, including identification of genistein. |
| PubMed:Determination of urinary lignans and phytoestrogen metabolites, potential antiestrogens and anticarcinogens, in urine of women on various habitual diets. |
| PubMed:Identification of lignans and phytoestrogens in urine of chimpanzees. |
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O-Desmethylangolensin (ODMA) is a metabolite of the soy isoflavone daidzein by intestinal bacteria in approximately 80-90% of persons. Studies suggest beneficial health effects associated with daidzein-metabolizing phenotypes, and there is some small association between ODMA production and some phenotypes. Few dietary factors are associated with daidzein-metabolizing phenotypes. However, it remains unclear why some, but not all, persons harbor ODMA-producing bacteria. ODMA production is inversely associated with age, height, weight, and body mass index. In addition, Asians are less likely than whites to be ODMA producers, and former smokers were more likely than never smokers to be ODMA producers. Investigators have attempted to identify the bacteria involved in ODMA production, and several candidate bacteria were associated, but not definitely identified. ODMA production is correlated with the abundance of methanogens, indicating that the metabolic fate of daidzein may be related to intestinal H(2) metabolism. (PMID: 18326607, 17506823) [HMDB]
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3D/inchi