EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

aromadedrin
dihydrokaempferol

Supplier Sponsors

Name:(2R,3R)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
CAS Number: 480-20-6Picture of molecule3D/inchi
Other(deleted CASRN):20257-56-1
FDA UNII: 7YA4640575
Nikkaji Web:J12.461C
MDL:MFCD00189454
XlogP3-AA:1.80 (est)
Molecular Weight:288.25584000
Formula:C15 H12 O6
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 638.00 to 639.00 °C. @ 760.00 mm Hg
Flash Point: 477.00 °F. TCC ( 247.22 °C. )
logP (o/w): 2.860 (est)
Soluble in:
 alcohol
 water, 2.136e+004 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Aromadedrin 98%
BOC Sciences
For experimental / research use only.
Aromadedrin
Carbosynth
For experimental / research use only.
Dihydrokaempferol
Coompo
For experimental / research use only.
Aromadedrin from Plants ≥95%
Sigma-Aldrich: Sigma
For experimental / research use only.
Aromadedrin ≥95% (LC/MS-ELSD)
sds
 
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:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for aromadedrin usage levels up to:
 not for fragrance use.
 
Recommendation for aromadedrin flavor usage levels up to:
 not for flavor use.
 
Safety References:
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 :122850
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(2R,3R)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
Chemidplus:0000480206
 
References:
 (2R,3R)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):122850
Pubchem (sid):135078176
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C00974
HMDB (The Human Metabolome Database):HMDB30847
FooDB:FDB012431
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 cherry sour cherry plant
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 cherry sweet cherry
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 oregano leaf
Search Trop Picture
 oregano plant
Search Trop Picture
 pinus sibirica wood
Search Trop Picture
 plum wood
Search Trop Picture
 tea shoot
Search Trop Picture
 
Synonyms:
 aromadendrin
 aromadendrol
(2R-trans)-2,3-dihydro-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
 dihydrokaempferol
(2R,3R)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
 

Articles:

PubMed:Insight into the role of anthocyanin biosynthesis-related genes in Medicago truncatula mutants impaired in pigmentation in leaves.
PubMed:Quantification of the production of dihydrokaempferol by flavanone 3-hydroxytransferase using capillary electrophoresis.
PubMed:Cymbidium hybrida dihydroflavonol 4-reductase does not efficiently reduce dihydrokaempferol to produce orange pelargonidin-type anthocyanins.
PubMed:Flavonoids with antimicrobial activity from the stem bark of Commiphora pedunculata (Kotschy & Peyr.) Engl.
PubMed:Direct comparison between genomic constitution and flavonoid contents in Allium multiple alien addition lines reveals chromosomal locations of genes related to biosynthesis from dihydrokaempferol to quercetin glucosides in scaly leaf of shallot (Allium cepa L.).
PubMed:Dihydrokaempferol as precursor for catechins in the tea plant.
PubMed:[Synthesis of dihydrokaempferol tetramethyl ether].
PubMed:Functional characterization of a Plagiochasma appendiculatum flavone synthase I showing flavanone 2-hydroxylase activity.
PubMed:Anti-HIV-1 activities of extracts and phenolics from Smilax china L.
PubMed:Examination of 1-methylimidazole series ionic liquids in the extraction of flavonoids from Chamaecyparis obtuse leaves using a response surface methodology.
PubMed:Expression analysis of dihydroflavonol 4-reductase genes in Petunia hybrida.
PubMed:Evolution of phenolic compounds and sensory in bottled red wines and their co-development.
PubMed:Inhibitory Effects of Chemical Compounds Isolated from the Rhizome of Smilax glabra on Nitric Oxide and Tumor Necrosis Factor- α Production in Lipopolysaccharide-Induced RAW264.7 Cell.
PubMed:Anticancer properties of extracts from Opuntia humifusa against human cervical carcinoma cells.
PubMed:Phenolic derivatives from Ruprechtia polystachya and their inhibitory activities on the glucose-6-phosphatase system.
PubMed:[Flavonoids from root of Machilus wangchiana].
PubMed:In vivo evolution of metabolic pathways by homeologous recombination in mitotic cells.
PubMed:Isolation of dihydroflavonol 4-reductase cDNA clones from Angelonia x angustifolia and heterologous expression as GST fusion protein in Escherichia coli.
PubMed:Nonanthocyanin secondary metabolites of black raspberry (Rubus occidentalis L.) fruits: identification by HPLC-DAD, NMR, HPLC-ESI-MS, and ESI-MS/MS analyses.
PubMed:Differential expression of flavonoid 3'-hydroxylase during fruit development establishes the different B-ring hydroxylation patterns of flavonoids in Fragaria × ananassa and Fragaria vesca.
PubMed:[Study on the chemical constituents of the PTP 1B inhibitory effective parts of Paeoniae Rubra Radix].
PubMed:Study on the correlation between constituents detected in serum from Rhizoma Smilacis Glabrae and the reduction of uric acid levels in hyperuricemia.
PubMed:Examination of the phenolic profile and antioxidant activity of the leaves of the Australian native plant Smilax glyciphylla.
PubMed:Isolation and functional analysis of a homolog of flavonoid 3',5'-hydroxylase gene from Pericallis × hybrida.
PubMed:[Chemical constituents of Cudrania cochinchinensis].
PubMed:Regiospecific modifications of naringenin for astragalin production in Escherichia coli.
PubMed:Tyrosinase inhibitory constituents from the bark of Peltophorum dasyrachis (yellow batai).
PubMed:Molecular cloning and characterization of three genes encoding dihydroflavonol-4-reductase from Ginkgo biloba in anthocyanin biosynthetic pathway.
PubMed:Flower colour and cytochromes P450.
PubMed:Divergent evolution of flavonoid 2-oxoglutarate-dependent dioxygenases in parsley.
PubMed:Anticomplement and antimicrobial activities of flavonoids from Entada phaseoloides.
PubMed:Cloning, characterization, and activity analysis of a flavonol synthase gene FtFLS1 and its association with flavonoid content in tartary buckwheat.
PubMed:Isolation, characterization, and function analysis of a flavonol synthase gene from Ginkgo biloba.
PubMed:Contribution of flavonoids and catechol to the reduction of ICAM-1 expression in endothelial cells by a standardised Willow bark extract.
PubMed:Production of 7-O-methyl aromadendrin, a medicinally valuable flavonoid, in Escherichia coli.
PubMed:Flavonoids from acai (Euterpe oleracea Mart.) pulp and their antioxidant and anti-inflammatory activities.
PubMed:Identification and quantification of phenolic compounds from pomegranate (Punica granatum L.) peel, mesocarp, aril and differently produced juices by HPLC-DAD-ESI/MS(n).
PubMed:Phenolic tyrosinase inhibitors from the stems of Cudrania cochinchinensis.
PubMed:Distribution and biosynthesis of flavan-3-ols in Camellia sinensis seedlings and expression of genes encoding biosynthetic enzymes.
PubMed:Antimicrobial biflavonoids from the aerial parts of Ouratea sulcata.
PubMed:[Studies on flavonoids from the leaves of Lindera aggregata].
PubMed:[Phenolic constituents from stem bark of Morus wittiorum and their anti-inflammation and cytotoxicity].
PubMed:Investigation of phenolic leaf extract of Heimia myrtifolia (Lythraceae): Pharmacological properties (stimulation of mineralization of SaOS-2 osteosarcoma cells) and identification of polyphenols.
PubMed:Cloning and characterization of a functional flavanone-3ß-hydroxylase gene from Medicago truncatula.
PubMed:Structural investigation of biologically active phenolic compounds isolated from European tree species.
PubMed:[Chemical constituents of rhizomes of Smilax ferox].
PubMed:Three new compounds from Morus nigra L.
PubMed:Flavonol synthase from Citrus unshiu is a bifunctional dioxygenase.
PubMed:A new petunia flower colour generated by transformation of a mutant with a maize gene.
PubMed:Purification and characterization of (2S)-flavanone 3-hydroxylase from Petunia hybrida.
PubMed:Preliminary investigation of naringenin hydroxylation with recombinant E. coli expressing plant flavonoid hydroxylation gene.
PubMed:Cloning and characterization of a UV-B-inducible maize flavonol synthase.
PubMed:Interactions between thrombin and natural products of Millettia nitita var. hirsutissima using capillary zone electrophoresis.
PubMed:[Studies on chemical constituents of rhizomes of Smilax china].
PubMed:Phenylpropanoid glycosyltransferases from osage orange (Maclura pomifera) fruit.
PubMed:Isolation and characterization of novel benzoates, cinnamates, flavonoids, and lignans from Riesling wine and screening for antioxidant activity.
PubMed:Alteration of a single amino acid changes the substrate specificity of dihydroflavonol 4-reductase.
PubMed:Enzymatic conversion of dihydroflavonols to flavan-3,4-diols using flower extracts of Dianthus caryophyllus L. (carnation).
PubMed:Modification of the B-ring during flavonoid synthesis in Petunia hybrida: Effect of the hydroxylation gene Hf1 on dihydroflavonol intermediates.
PubMed:The B-ring hydroxylation pattern of intermediates of anthocyanin synthesis in pelargonidin-and cyanidin-producing lines of Matthiola incana.
PubMed:Anthocyanin synthesis in a white flowering mutant of Petunia hybrida : II. Accumulation of dihydroflavonol intermediates in white flowering mutants; uptake of intermediates in isolated corollas and conversion into anthocyanins.
PubMed:Flavonoid-3',5'-hydroxylase from Phalaenopsis: a novel member of cytochrome P450s, its cDNA cloning, endogenous expression and molecular modeling.
PubMed:Structural and mechanistic studies on anthocyanidin synthase catalysed oxidation of flavanone substrates: the effect of C-2 stereochemistry on product selectivity and mechanism.
PubMed:Molecular and biochemical analysis of two cDNA clones encoding dihydroflavonol-4-reductase from Medicago truncatula.
PubMed:Accumulation of flavonols in response to ultraviolet-B irradiation in soybean is related to induction of flavanone 3-beta-hydroxylase and flavonol synthase.
PubMed:Antibacterial phenolic compounds from the spines of Gleditsia sinensis Lam.
PubMed:Crystal structure of grape dihydroflavonol 4-reductase, a key enzyme in flavonoid biosynthesis.
PubMed:[Studies on chemical constituents of Smilax china].
PubMed:Mechanistic studies on three 2-oxoglutarate-dependent oxygenases of flavonoid biosynthesis: anthocyanidin synthase, flavonol synthase, and flavanone 3beta-hydroxylase.
PubMed:An allele of dihydroflavonol 4-reductase associated with the ability to produce red anthocyanin pigments in potato (Solanum tuberosum L.).
PubMed:Characterization and content of flavonoid glycosides in genetically modified tomato (Lycopersicon esculentum) fruits.
PubMed:Study of low molecular weight phenolic compounds during the aging of sparkling wines manufactured with red and white grape varieties.
PubMed:Pigmentation in the developing seed coat and seedling leaves of Brassica carinata is controlled at the dihydroflavonol reductase locus.
PubMed:Isolation and characterization of a flavonoid 3'-hydroxylase cDNA clone corresponding to the Ht1 locus of Petunia hybrida.
PubMed:[Study on flavonoids in seeds of Hovenia dulcis].
PubMed:Purification and characterization of (+)dihydroflavonol (3-hydroxyflavanone) 4-reductase from flowers of Dahlia variabilis.
PubMed:Induction and characterization of a microsomal flavonoid 3'-hydroxylase from parsley cell cultures.
PubMed:Chemical constituents of Echites hirsuta (Apocynaceae).
PubMed:Modification of the B-ring during flavonoid synthesis in Petunia hybrida: Introduction of the 3'-hydroxyl group regulated by the gene Ht1.
PubMed:Flavonoids and other chemical constituents of fossil miocene zelkova (ulmaceae).
PubMed:Biochemical and genetic characterization of Arabidopsis flavanone 3beta-hydroxylase.
PubMed:An early gene of the flavonoid pathway, flavanone 3-hydroxylase, exhibits a positive relationship with the concentration of catechins in tea (Camellia sinensis).
PubMed:Implications of long-distance flavonoid movement in Arabidopsis thaliana.
PubMed:Flavanone 3beta-hydroxylases from rice: key enzymes for favonol and anthocyanin biosynthesis.
PubMed:Isolation of flavonoids from aspen knotwood by pressurized hot water extraction and comparison with other extraction techniques.
PubMed:Flavonoids are differentially taken up and transported long distances in Arabidopsis.
PubMed:Production of red-flowered plants by genetic engineering of multiple flavonoid biosynthetic genes.
PubMed:Monoamine oxidase inhibitory components from Cayratia japonica.
PubMed:Redirection of anthocyanin synthesis in Osteospermum hybrida by a two-enzyme manipulation strategy.
PubMed:Bioactive constituents of Spatholobus suberectus in regulating tyrosinase-related proteins and mRNA in HEMn cells.
PubMed:Constituents of the stems and fruits of Opuntia ficus-indica var. saboten.
PubMed:Inhibitory activity of flavonoids from Prunus davidiana and other flavonoids on total ROS and hydroxyl radical generation.
PubMed:Phenolic extractives in Salix caprea wood and knots.
PubMed:Metabolite profiling of tomato (Lycopersicon esculentum) using 1H NMR spectroscopy as a tool to detect potential unintended effects following a genetic modification.
PubMed:Functional expression and mutational analysis of flavonol synthase from Citrus unshiu.
PubMed:In vitro properties of a recombinant flavonol synthase from Arabidopsis thaliana.
PubMed:Flavonoids and UV photoprotection in Arabidopsis mutants.
PubMed:[Studies on the chemical constituents of Rhodiola fastigita].
PubMed:Cloning of cDNA coding for dihydroflavonol-4-reductase (DFR) and characterization of dfr expression in the corollas of Gerbera hybrida var. Regina (Compositae).
PubMed:Purification and characterization of flavone synthase I, a 2-oxoglutarate-dependent desaturase.
PubMed:Enzymatic reduction of (+)-dihydroflavonols to flavan-3,4-cis-diols with flower extracts from Matthiola incana and its role in anthocyanin biosynthesis.
PubMed:Genetic and biochemical studies on flavonoid 3'-hydroxylation in flowers of Petunia hybrida.
PubMed:Leucoanthocyanidins as intermediates in anthocyanidin biosynthesis in flowers of Matthiola incana R. Br.
PubMed:Chalcone synthesis and hydroxylation of flavonoids in 3'-position with enzyme preparations from flowers of Dianthus caryophyllus L. (carnation).
 
Notes:
inhibits protein kinase c; the dihydro makes it a flavone rather than a flavonol. Isol. from Citrus spp. and many other plants
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