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About This Item
Empirical Formula (Hill Notation):
C20H16O
CAS Number:
Molecular Weight:
272.34
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Assay
98%
mp
142-144 °C (lit.)
functional group
hydroxyl
SMILES string
OC1CCCc2c1cc3ccc4cccc5ccc2c3c45
InChI
1S/C20H16O/c21-18-6-2-5-15-16-10-9-13-4-1-3-12-7-8-14(11-17(15)18)20(16)19(12)13/h1,3-4,7-11,18,21H,2,5-6H2
InChI key
VKUQFYXBPGXTKI-UHFFFAOYSA-N
General description
7,8,9,10-Tetrahydrobenzo[a]pyren-7-ol (7-hydroxy-7,8,9,10-tetrahydrobenzo[a]pyrene), a polycyclic aromatic hydrocarbon (PAH), is a substituted benzopyrene. Its bromination reaction with N-bromosaccharin (NBSac) has been investigated. The sulfotransferase-assisted activation of 7-hydroxy-7,8,9,10-tetrahydrobenzo[a]pyrene to form electrophilic, mutagenic, or tumorigenic sulfuric acid ester metabolite, which binds covalently to DNA and leads to mutation, has been reported.
Application
7,8,9,10-Tetrahydrobenzo[a]pyren-7-ol may be used as a starting material in the synthesis of (±)-trans-7,8-dihydroxy-6-fluoro-7,8-dihydrobenzo[a]pyrene.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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Y J Surh et al.
Chemical research in toxicology, 8(5), 693-698 (1995-07-01)
Some hydroxymethyl-substituted polycyclic aromatic hydrocarbons have been shown to be converted to electrophilic, mutagenic, or tumorigenic sulfuric acid ester metabolites by cytosolic sulfotransferase activity in rodent liver. Likewise, certain types of aromatic compounds with a secondary alcoholic functional group at
V Heisig et al.
Science (New York, N.Y.), 223(4633), 289-291 (1984-01-20)
The laser excited fluorescence-line-narrowed spectrum of DNA modified with (+/-)-r-7,t-8-dihydroxy-t-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (BPDE), the ultimate carcinogenic metabolite of benzo[a]pyrene (BP), has been obtained in a water-glycerol-ethanol glass at 4.2 K. The spectrum was well resolved and highly characteristic of the chromophore. Comparisons
Recent Progress in the Use of N-Halo Compounds in Organic Synthesis.
Veisi H, et al.
Organic preparations and procedures international, 43(6), 489-540 (2011)
Barbara Zajc
The Journal of organic chemistry, 64(6), 1902-1907 (2001-10-25)
Synthesis of (+/-)-trans-7,8-dihydroxy-6-fluoro-7,8-dihydrobenzo[a]pyrene, the metabolite from 6-fluoro-benzo[a]pyrene, is described. Position 6 of 7,8,9,10-tetrahydrobenzo[a]pyren-7-ol (1) was functionalized by bromination with N-bromosaccharin. Regioselectivity in the bromination is thought to derive from a substrate-reagent hydrogen bond. NMR evidence is offered to support this
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