pentacyclo[10.6.2.02,7.09,19.016,20]icosa-1(18),2,4,6,8,10,12,14,16,19-decaene

• ChemBase ID: 126079
• Molecular Formular: C20H12
• Molecular Mass: 252.30928
• Monoisotopic Mass: 252.09390038
• SMILES: c1ccc2c(c1)cc1ccc3cccc4c3c1c2cc4
• Canonical SMILES: c1ccc2c(c1)c1ccc3c4c1c(c2)ccc4ccc3
• InChI: InChI=1S/C20H12/c1-2-7-17-15(4-1)12-16-9-8-13-5-3-6-14-10-11-18(17)20(16)19(13)14/h1-12H
• InChIKey: FMMWHPNWAFZXNH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: pentacyclo[10.6.2.0^2,^7.0^9,^1^9.0^1^6,^2^0]icosa-1(18),2,4,6,8,10,12,14,16,19-decaene; pentacyclo[10.6.2.0^2,^7.0^9,^1^9.0^1^6,^2^0]icosa-1(18),2(7),3,5,8,10,12,14,16,19-decaene
• IUPAC Traditional name: benzopyrene; pentacyclo[10.6.2.0^2,^7.0^9,^1^9.0^1^6,^2^0]icosa-1(18),2(7),3,5,8,10,12,14,16,19-decaene
• Synonyms: Benzo[a]pyrene; 3,4-Benz[a]pyrene; 4,5-Benzpyrene; 6,7-Benzopyrene; BaP; Benz[a]pyrene; Benzo[d,e,f]chrysene; Benzopyrene; NSC 21914; Benzopyrene; Benzo(a)pyrene; Benzo[a]pyrene solution; 3,4-Benzopyrene; 3,4-Benzpyrene; Benzo[def]chrysene; Benzo[a]pyrene; Benzo[pqr]tetraphene; 苯并[a]芘 溶液; 3,4-苯并芘; 苯并[det]屈; 苯并芘; 苯并[a]芘

Database IDs

• CAS Number: 50-32-8
• EC Number: 200-028-5
• MDL Number: MFCD00003602
• Beilstein Number: 1911333
• Merck Index: 141103
• PubChem SID: 24891610; 162220420; 24872109; 24862983
• PubChem CID: 2336
• CHEBI ID: 29865
• CHEMBL: 31184
• Chemspider ID: 2246
• KEGG ID: C07535
• Wikipedia Title: Benzo(a)pyrene

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 5.273404
• LogD (pH = 7.4): 5.273404
• Log P: 5.273404
• Molar Refractivity: 83.1728 cm^3
• Polarizability: 37.737247 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 0.11 mg/L (25 °C) in water; Chloroform; Soluble in benzene, toluene, and xylene. Sparingly soluble in alcohol, methanol. Insoluble in water
• Apperance: Crystalline; Yellow Solid
• Melting Point: 174-176°C; 177-180 °C(lit.); 177-180°C; 179 °C
• Boiling Point: 495 °C; 495 °C(lit.); 495°C
• Flash Point: -.4 °F; -18 °C
• Density: 1.24 g/cm3 (25 °C)

Safety Information

• Storage Condition: Refrigerator
• RTECS: DJ3675000
• European Hazard Symbols: Flammable (F); Nature polluting (N); Toxic (T)
• UN Number: 1145; 3077; UN3077
• German water hazard class: 3
• Hazard Class: 3; 9
• Packing Group: 2; 3; III
• Risk Statements: 45-11-38-50/53-65-67; 45-46-60-61-43-50/53
• Safety Statements: 53-16-45-61-62; 53-45-60-61
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS07; GHS08; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H304-H315-H336-H350-H410; H317-H340-H350-H360FD-H410; H340-H350-H360-H400-H410-H317
• GHS Precautionary statements: P201-P210-P261-P273-P301 + P310-P308 + P313; P201-P273-P280-P308 + P313-P501; P261-P280-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1145 3/PG 2; UN 3077 9/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥96% (HPLC); 96%; 97%
• Concentration: 100 ng/μL in cyclohexane
• Grade: analytical standard, for environmental analysis; certified reference material; TraceCERT®
• Packaging: pkg of 100 mg
• Empirical Formula (Hill Notation): C20H12

DETAILS

Sigma Aldrich - B1760

Biochem/physiol Actions
A polycyclic aromatic hydrocarbon (PAH), environmental pollutant and carcinogen. Used as a chemical carcinogen in experimental models of cancer. Carcinogenesis depends on it′s oxidation by CYP1A1 to benzo[a]pyrenediolepoxide, that forms depurinating adducts with DNA that dissociate to form abasic lesions. Benzo[a]pyrene is a ligand for the arylhydrocarbon receptor (AhR), and some of its biological effects, including the induction of CYP1A1, appear to be mediated via activation of the AhR.

Sigma Aldrich - 31306

Caution
Restricted to professional users. Attention - Avoid exposure.

Sigma Aldrich - 51968

General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - B205800

Benzopyrene is a polyaromatic hydrocarbon (PAH) found in coal tar. Benzopyrene is a known carcinogen. The metbolism of Benzopyrene results in diol epoxides that react and bind to DNA forming adducts which in turns leads to mutations and eventually cancer.

REFERENCES

• Arif, J. et al.: DNA Adducts, 127 (2010)
• Nair, S. et al.: Cancer Prev. Res., 2, 895 (2010)
• Staal, Y. et al.: Carcinogenesis, 27, 646 (2010)
• Mensing, T. et al.: Int. Hyg. Env. Health, 208, 197 (2010)