2-hydroxy-6-oxo-6-phenyl hexa-2,4-dienoate
2,4-hexadienoic acid, 2-hydroxy-6-oxo-6-phenyl-
 
Notes:
metabolic product of biphenyl; from pseudomonas putida.
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CAS Number: 50480-67-6Picture of molecule3D/inchi
XlogP3-AA: 1.80 (est)
Molecular Weight: 218.20850000
Formula: C12 H10 O4
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Category: natural substances and extractives
 
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 401.23 °C. @ 760.00 mm Hg (est)
Flash Point: 411.00 °F. TCC ( 210.60 °C. ) (est)
logP (o/w): 1.189 (est)
Soluble in:
 water, 5542 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
 None found
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Safety Information:
 
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
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for 2-hydroxy-6-oxo-6-phenyl hexa-2,4-dienoate usage levels up to:
 not for fragrance use.
 
Recommendation for 2-hydroxy-6-oxo-6-phenyl hexa-2,4-dienoate flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Cancer Citations: Search
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EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 5462192
National Institute of Allergy and Infectious Diseases: Data
 (3E,5Z)-6-hydroxy-2-oxo-6-phenylhexa-3,5-dienoic acid
Chemidplus: 0050480676
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References:
 (3E,5Z)-6-hydroxy-2-oxo-6-phenylhexa-3,5-dienoic acid
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 5462192
Pubchem (sid): 135074299
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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
HMDB (The Human Metabolome Database): Search
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 pseudomonas putida
Search  PMC Picture
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Synonyms:
2,4-hexadienoic acid, 2-hydroxy-6-oxo-6-phenyl-
 HOPDA
(3E,5Z)-6-hydroxy-2-oxo-6-phenylhexa-3,5-dienoic acid
2-hydroxy-6-oxo-6-phenyl-2,4-hexadienoic acid
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Articles:
PubMed: Mechanism-based inhibition of HsaD: a C-C bond hydrolase essential for survival of Mycobacterium tuberculosis in macrophage.
PubMed: A substrate-assisted mechanism of nucleophile activation in a Ser-His-Asp containing C-C bond hydrolase.
PubMed: The lid domain of the MCP hydrolase DxnB2 contributes to the reactivity toward recalcitrant PCB metabolites.
PubMed: Single residues dictate the co-evolution of dual esterases: MCP hydrolases from the α/β hydrolase family.
PubMed: The key role of a non-active-site residue Met148 on the catalytic efficiency of meta-cleavage product hydrolase BphD.
PubMed: The catalytic serine of meta-cleavage product hydrolases is activated differently for C-O bond cleavage than for C-C bond cleavage.
PubMed: Potential for biodegradation of polychlorinated biphenyls (PCBs) by Sinorhizobium meliloti.
PubMed: Flow cytometry-based method for isolating live bacteria with meta-cleavage activity on dihydroxy compounds of biphenyl.
PubMed: Characterization of a carbon-carbon hydrolase from Mycobacterium tuberculosis involved in cholesterol metabolism.
PubMed: Characterization and functional analysis of a novel gene cluster involved in biphenyl degradation in Rhodococcus sp. strain R04.
PubMed: The molecular basis for inhibition of BphD, a C-C bond hydrolase involved in polychlorinated biphenyls degradation: large 3-substituents prevent tautomerization.
PubMed: The tautomeric half-reaction of BphD, a C-C bond hydrolase. Kinetic and structural evidence supporting a key role for histidine 265 of the catalytic triad.
PubMed: Characterization of a C-C bond hydrolase from Sphingomonas wittichii RW1 with novel specificities towards polychlorinated biphenyl metabolites.
PubMed: Temperature-dependent biotransformation of 2,4'-dichlorobiphenyl by psychrotolerant Hydrogenophaga strain IA3-A: higher temperatures prevent excess accumulation of problematic meta-cleavage products.
PubMed: Kinetic and structural insight into the mechanism of BphD, a C-C bond hydrolase from the biphenyl degradation pathway.
PubMed: Structures of ternary complexes of BphK, a bacterial glutathione S-transferase that reductively dechlorinates polychlorinated biphenyl metabolites.
PubMed: A glutathione S-transferase catalyzes the dehalogenation of inhibitory metabolites of polychlorinated biphenyls.
PubMed: Expression and homology modeling of 2-aminobiphenyl-2,3-diol-1,2-dioxygenase from Pseudomonas stutzeri carbazole degradation pathway.
PubMed: Characterization of the putative operon containing arylamine N-acetyltransferase (nat) in Mycobacterium bovis BCG.
PubMed: Purification, characterization, and steady-state kinetics of a meta-cleavage compound hydrolase from Pseudomonas fluorescens IPO1.
PubMed: Diversity of 2,3-dihydroxybiphenyl dioxygenase genes in a strong PCB degrader, Rhodococcus sp. strain RHA1.
PubMed: Biodegradation of dibenzo-p-dioxin, dibenzofuran, and chlorodibenzo-p-dioxins by Pseudomonas veronii PH-03.
PubMed: Crystal structure of a histidine-tagged serine hydrolase involved in the carbazole degradation (CarC enzyme).
PubMed: Comparative specificities of two evolutionarily divergent hydrolases involved in microbial degradation of polychlorinated biphenyls.
PubMed: Expression of the bph genes involved in biphenyl/PCB degradation in Pseudomonas sp. KKS102 induced by the biphenyl degradation intermediate, 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid.
PubMed: Versatile transcription of biphenyl catabolic bph operon in Pseudomonas pseudoalcaligenes KF707.
PubMed: Degradation of anaerobic reductive dechlorination products of Aroclor 1242 by four aerobic bacteria.
PubMed: Characterization of the pcbE gene encoding 2-hydroxypenta-2,4-dienoate hydratase in Pseudomonas sp. DJ-12.
PubMed: Identification of a serine hydrolase as a key determinant in the microbial degradation of polychlorinated biphenyls.
PubMed: Purification and preliminary characterization of a serine hydrolase involved in the microbial degradation of polychlorinated biphenyls.
PubMed: Two nearly identical aromatic compound hydrolase genes in a strong polychlorinated biphenyl degrader, Rhodococcus sp. strain RHA1.
PubMed: The bphDEF meta-cleavage pathway genes involved in biphenyl/polychlorinated biphenyl degradation are located on a linear plasmid and separated from the initial bphACB genes in Rhodococcus sp. strain RHA1.
PubMed: Location and sequence analysis of a 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase-encoding gene (bpdF) of the biphenyl/polychlorinated biphenyl degradation pathway in Rhodococcus sp. M5.
PubMed: Genetic analysis of a Pseudomonas locus encoding a pathway for biphenyl/polychlorinated biphenyl degradation.
PubMed: Gene components responsible for discrete substrate specificity in the metabolism of biphenyl (bph operon) and toluene (tod operon).
PubMed: Purification of two isofunctional hydrolases (EC 3.7.1.8) in the degradative pathway for dibenzofuran in Sphingomonas sp. strain RW1.
PubMed: 3-(2-hydroxyphenyl)catechol as substrate for proximal meta ring cleavage in dibenzofuran degradation by Brevibacterium sp. strain DPO 1361.
PubMed: Identification and localization of 3-phenylcatechol dioxygenase and 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase genes of Pseudomonas putida and expression in Escherichia coli.
PubMed: Cloning of bacterial genes specifying degradation of 4-chlorobiphenyl from Pseudomonas putida OU83.
PubMed: Metabolism of biphenyl. 2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoate: the meta-cleavage product from 2,3-dihydroxybiphenyl by Pseudomonas putida.
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