All Photos(1)
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)[1], is a substituted benzopyrene. Its bromination reaction with N-bromosaccharin (NBSac) has been investigated.[2] 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.[1]
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.[3]
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Choose from one of the most recent versions:
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
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
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)
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
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
Active Filters
Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.
Contact Technical Service
