Benzo(a)pyrene

Names

[ CAS No. ]:
50-32-8

[ Name ]:
Benzo(a)pyrene

[Synonym ]:
UNII-3417WMA06D
Benzo[a]pyrene (Ames grade)
Benzo[A]Pyrene
Benzo(d,e,f)chrysene
Benzo(a)pyrene
Benzo[a]pyren
benzo[1,2,5]thiadiazole-4-sulfonyl chloride
2,1,3-benzothiadiazol-4-sulfonyl chloride
3,4-Benzpyrene
3,4-Benz(a)pyrene
4,5-BENZPYRENE
2,1,3-Benzothiadiazole,4-chlorosulfonyl
3,4-benzopyrene
2,1,3-benzothiadiazole-4-sulphonyl chloride
1,2-Benzpyrene (VAN)
Benzo[pqr]tetraphene
Benzopyrene
4-Chlorosulfonyl-2,1,3-benzothiadiazole
2,1,3-benzothiadiazole-4-sulfonylchloride
3,4-Benzo(a)pyrene
Benzo-2,1,3-thiadiazole-4-sulphonyl chloride
Benzo[c][1,2,5]thiadiazole-4-sulfonyl chloride
EINECS 200-028-5
benz[a]pyrene
benzo[2,1,3]thiadiazole-4-sulfonyl chloride
6,7-Benzopyrene
MFCD00003602
1,2-Benzpyrene

Biological Activity

[Description]:

Benzo[a]pyrene shows lung carcinogenicity in animal models, and it is frequently used in chemoprevention studies.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Cancer

[In Vivo]

Statistically significant decrease is observed at 7 weeks in females receiving 1.0 mg Benzo[a]pyrene (B[a]P) compare with the vehicle group. As lung tumorigenesis induced by Benzo[a]pyrene is dose dependent in female A/J mice. The incidence of hyperplasia values in females treating with 0.25, 0.50, and 1.0 mg Benzo[a]pyrene are significantly higher than in the vehicle-treated group. The incidence of adenoma in females receiving 1.0 mg Benzo[a]pyrene is significantly higher than in the vehicle group. The multiplicity of hyperplasia in females receiving 0.50 or 1.0 mg Benzo[a]pyrene is significantly higher than in the vehicle group. The multiplicity of adenoma in the group treated with 1.0 mg is also significantly higher than in the vehicle group. The incidences of hyperplasia and adenoma in female A/J mice are significantly increased by Benzo[a]pyrene in a dose-dependent manner[1]. Benzo[a]pyrene induces an average of 9.38±1.75 tumors with an average tumor load of 19.53±3.81 mm3 (P<0.05 compare to control). Benzo[a]pyrene administration significantly (P<0.05) decreases cAMP levels in tumors with adjacent lung tissues. The expression level of PDE4D gene is also increased by Benzo[a]pyrene administration[2].

[Animal admin]

Female A/J mice are randomized into eight groups (n=8): (i) control; (ii)Benzo[a]pyrene (B(a)P)+vehicle (methocel); (iii) Benzo[a]pyrene+roflumilast 1 mg/kg; (iv) Benzo[a]pyrene+roflumilast 5 mg/kg; (v) Benzo[a]pyrene+aerozolie phosphate-buffer saline (PBS); (vi) Benzo[a]pyrene+aerosolize budesonide 2.25 mg/mL; (vii) Benzo[a]pyrene+aerosolized budesonide 2.25 mg/mL+roflumilast 1 mg/kg; and (viii) Benzo[a]pyrene+aerosolize budesonide 2.25 mg/mL+roflumilast 5 mg/kg groups. A single dose of Benzo[a]pyrene in corn oil is given intraperitoneally once at 100 mg/kg body weight. Roflumilast (1 or 5 mg/kg) is started 2 weeks after Benzo[a]pyrene. It is continued for 26 weeks (3 days/week) via oral gavage. Mice in the Benzo[a]pyrene+vehicle group are treated with an equal volume of methocel as solvent control. Aerosolizing budesonide is administrated by inhaling route as an aerosol at a dose of 2.25 mg/mL for 2 min per application at 2 weeks after Benzo[a]pyrene. It is continued for 26 weeks (5 days/week). PBS is also used as solvent control by inhaling route after Benzo[a]pyrene administration in the Benzo[a]pyrene+PBS group. Mice are killed at 28 weeks after exposure to Benzo[a]pyrene. Their lungs are excised and stored at -70 °C[2].

[References]

[1]. Saeko Onami, et al. Dosimetry for lung tumorigenesis induced by urethane, 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone (NNK), and benzo[a]pyrene (B[a]P) in A/JJmsSlc mice. J Toxicol Pathol. 2017 Jul; 30(3): 209–216.

[2]. Yeo CD, et al. Roflumilast treatment inhibits lung carcinogenesis in benzo(a)pyrene-induced murine lung cancer model. Eur J Pharmacol. 2017 Oct 5;812:189-

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
495.0±0.0 °C at 760 mmHg

[ Melting Point ]:
177-180°C

[ Molecular Formula ]:
C₂₀H₁₂

[ Molecular Weight ]:
252.309

[ Flash Point ]:
228.6±13.7 °C

[ Exact Mass ]:
252.093903

[ LogP ]:
6.40

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.887

[ Stability ]:
Stable. Incompatible with strong oxidizing agents.

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07, GHS08, GHS09

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H317-H340-H350-H360FD-H410

[ Supplemental HS ]:
Repeated exposure may cause skin dryness or cracking.

[ Precautionary Statements ]:
P201-P273-P280-P308 + P313-P333 + P313-P501

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ Hazard Codes ]:
F:Flammable;T:Toxic;

[ Risk Phrases ]:
R45;R11;R38;R50/53;R65;R67

[ Safety Phrases ]:
S45-S53-S61-S60-S26-S62

[ RIDADR ]:
2811

[ RTECS ]:
DJ3675000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1

[ HS Code ]:
2902909090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2902909090

[ Summary ]:
2902909090 other aromatic hydrocarbons。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:2.0%。General tariff:30.0%

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Related Compounds

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