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391611

7,8,9,10-Tetrahydrobenzo[a]pyren-7-ol

Name: 7,8,9,10-Tetrahydrobenzo[<I>a</I>]pyren-7-ol
Brand: ALDRICH

98%

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About This Item

Empirische Formel (Hill-System):

C₂₀H₁₆O

CAS-Nummer:

6272-55-5

Molekulargewicht:

272.34

MDL-Nummer:

MFCD00192475

UNSPSC-Code:

12352100

PubChem Substanz-ID:

24864391

NACRES:

NA.22

Assay

98%

mp (Schmelzpunkt)

142-144 °C (lit.)

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

InChIKey

VKUQFYXBPGXTKI-UHFFFAOYSA-N

Allgemeine Beschreibung

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.

Anwendung

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.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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Sulfotransferase-mediated activation of 7,8,9,10-tetrahydro-7-ol, 7,8-dihydrodiol, and 7,8,9,10-tetraol derivatives of benzo[a]pyrene.

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

Fluorescence-line-narrowed spectra of polycyclic aromatic carcinogen-DNA adducts.

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)

Synthesis of (+/-)-trans-7,8-Dihydrodiol of 6-Fluoro-benzo[a]pyrene via Hydroxyl-Directed Regioselective Functionalization of Substituted Pyrene.

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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