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Chemical structure of Benzo[a] pyrene | 50-32-8
CAS: 50-32-8
SKU: S2679
Benzo[a] pyrene | SKU: S2679
synonyms: BaP; 3,4-Benzopyrene; 3,4-Benzpyrene; Benzo[def]chrysene; Benz[a]pyrene
Chemical structure of Benzo[a] pyrene | 50-32-8
Benzo[a]pyrene (BaP, 3,4-benzopyrene, 3,4-benzpyrene; C20H12) is a five-ring polycyclic aromatic hydrocarbon (PAH) formed by the incomplete combustion of organic matter. It has a molecular weight of 252.31 g/mol and is supplied as a pale yellow crystalline solid with a melting point of 177–180 °C, a boiling point of about 495 °C and an assay of at least 96% by HPLC. BaP is the best-studied member of the PAH family and is used in two distinct ways. In analytical chemistry it is the indicator compound for PAH contamination: it is one of the 16 PAHs on the U.S. EPA priority-pollutant list and a regulatory marker for PAHs in air, water, soil and food, so laboratories need it to prepare calibration standards. In toxicology and cancer research it is a classic chemical carcinogen: it is oxidised by cytochrome P450 CYP1A1 to benzo[a]pyrene diol epoxide, which forms depurinating DNA adducts that leave abasic lesions, and it is a ligand of the aryl hydrocarbon receptor (AhR), through which it induces CYP1A1. Benzo[a]pyrene is a known human carcinogen (IARC Group 1), a germ-cell mutagen and a reproductive toxicant. Sarchem Labs provides benzo[a]pyrene (SKU S2679) solely for laboratory analytical and research use by trained personnel with suitable containment. It is not offered for consumer, food, cosmetic or any other non-laboratory use. A Certificate of Analysis and Safety Data Sheet accompany each lot.
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Specifications

Boiling Point495°C (lit.)
Melting Point177–180°C (lit.)
ColorUndesignated
Formula Weight252.32
Physical FormCrystal-Powder at 20°C
Chemical Name or MaterialBenzo[a]pyrene (3,4-benzopyrene, purified by sublimation)
UN Number3077
Molecular Weight252.31 g/mol
SMILES Stringc1ccc2c(c1)cc3ccc4cccc5ccc2c3c45
Assay≥96% (HPLC)
CAS Number50-32-8
EC Number200-028-5
NACRESNA.25
PubChem Substance ID24891610
UNSPSC Code12352005
MDL NumberMFCD00003602
InChI1S/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
InChI KeyFMMWHPNWAFZXNH-UHFFFAOYSA-N
PubChem CID2336
Beilstein/REAXYS Number1911333
Quality Level200
FormSolid (crystal-powder)
Empirical Formula (Hill Notation)C20H12

Applications

No Application Found
Carcinogenesis models: a reference chemical carcinogen in experimental models of cancer, including studies of DNA-adduct formation, mutagenesis and tumour initiation.
Xenobiotic metabolism research: a model substrate for cytochrome P450 CYP1A1 and CYP1B1 and for epoxide hydrolase, used to study metabolic activation to the diol epoxide.
AhR signalling: a ligand of the aryl hydrocarbon receptor used in studies of CYP1A1 induction and receptor-mediated toxicity.
Environmental and remediation research: a test PAH for biodegradation, photodegradation and sorption studies.

Product Description

What is Benzo[a]pyrene?

Benzo[a]pyrene is a planar polycyclic aromatic hydrocarbon of five fused rings, with the formula C20H12 and a molecular weight of 252.31 g/mol. It is poorly soluble in water, soluble in organic solvents such as toluene, dichloromethane and cyclohexane, and strongly fluorescent, which is the basis of its trace analysis. It is formed in coal tar, tobacco smoke, vehicle exhaust, charred or grilled food and other combustion products. It should not be confused with benzo[e]pyrene, benz[a]anthracene or pyrene, which are different PAHs with different CAS numbers and toxicity.

Uses of Benzo[a]pyrene

Environmental, food-safety and clinical laboratories use BaP as a calibration standard because it is the marker compound for PAH regulations. Toxicologists use it to induce and study chemical carcinogenesis, and biochemists use it to explore how the cell metabolises and detoxifies PAHs. Because of the hazards, most laboratories buy it as the neat solid only when they need to prepare their own stock solutions, and use certified solutions for routine work.

Regulatory and Compliance Considerations

Benzo[a]pyrene is classified by the International Agency for Research on Cancer as carcinogenic to humans (Group 1) and is one of the 16 PAHs on the U.S. EPA priority-pollutant list. Under the EU CLP system it is classified as carcinogenic (Category 1B), mutagenic (Category 1B) and toxic to reproduction (Category 1B), and it is identified as a substance of very high concern (PBT/vPvB). Purchasers are responsible for compliance with applicable laboratory-safety, chemical-control, transport and waste-disposal regulations.

Buying and Handling Considerations

The grade offered is at least 96% by HPLC. Ask for the Certificate of Analysis of the lot, and tell us if you need a certified reference material or a ready-made solution instead of the neat solid; both are available elsewhere and avoid handling the powder. Handle only in a fume hood, glove box or ventilated balance enclosure, with double gloves, a lab coat and eye protection, in a designated area. Store locked up in a tightly closed, light-protected container, and collect all waste, including contaminated gloves and wipes, as hazardous carcinogenic waste. The product ships under UN 3077 (environmentally hazardous substance, solid, n.o.s.).

Safety Information

  • Pictograms / Signal Word: GHS08 (health hazard), GHS07 (exclamation mark), GHS09 (environment) | Danger
  • Hazard Statements: H317 (may cause an allergic skin reaction), H340 (may cause genetic defects), H350 (may cause cancer), H360FD (may damage fertility; may damage the unborn child), H410 (very toxic to aquatic life with long lasting effects), EUH441 (strongly accumulates in the environment and living organisms)
  • Hazard Classification: Carc. 1B, Muta. 1B, Repr. 1B, Skin Sens. 1, Aquatic Acute 1, Aquatic Chronic 1, PBT, vPvB
  • Precautionary Statements: P201, P202, P273, P280, P308 + P313, P391, P501
  • Storage Class: 6.1C – Combustible acute toxic Cat. 3 / toxic compounds or compounds which cause chronic effects | Flash Point: not applicable
  • Transport: UN 3077

Obtain special instructions before use and do not handle until all safety precautions have been read and understood. Avoid all exposure, wear protective gloves and clothing, and do not release into the environment.

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FAQs: Benzo[a] pyrene

It is used as a calibration standard for PAH analysis in environmental and food samples and as a reference chemical carcinogen in toxicology and cancer research. It is supplied for laboratory use only.

Yes. It is classified by IARC as carcinogenic to humans (Group 1) and under EU CLP as a Category 1B carcinogen, a Category 1B mutagen and a Category 1B reproductive toxicant (H350, H340, H360FD).

The formula is C20H12, the molecular weight is 252.31 g/mol and the melting point is 177–180 °C. The assay is at least 96% by HPLC.

CYP1A1 oxidises it to benzo[a]pyrene diol epoxide, which binds DNA and forms adducts, including depurinating adducts that leave abasic sites. Those lesions can cause mutations if not repaired.

Only in a fume hood or glove box with double gloves, protective clothing and eye protection. Store it locked up, protected from light, and collect all contaminated waste as hazardous carcinogenic waste.

Yes, certified solutions and reference materials are available from reference-material suppliers and avoid weighing the neat solid. Ask Sarchem Labs about the format you need.

Yes. A Certificate of Analysis and Safety Data Sheet accompany each lot of SKU S2679, which is supplied only for laboratory analytical and research use by trained personnel.