pentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-1(14),2,4,6,8,10,12,15,17,19,21-undecaen-7-yl acetate

• ChemBase ID: 91061
• Molecular Formular: C24H16O2
• Molecular Mass: 336.38264
• Monoisotopic Mass: 336.11502975
• SMILES: O(c1ccc2c3cc4ccc5c(c4cc3ccc2c1)cccc5)C(=O)C
• Canonical SMILES: CC(=O)Oc1ccc2c(c1)ccc1c2cc2ccc3c(c2c1)cccc3
• InChI: InChI=1S/C24H16O2/c1-15(25)26-20-10-11-22-17(12-20)8-9-19-13-23-18(14-24(19)22)7-6-16-4-2-3-5-21(16)23/h2-14H,1H3
• InChIKey: YMQDQOSGAXDBMK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: pentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-1(14),2,4,6,8,10,12,15,17,19,21-undecaen-7-yl acetate; pentacyclo[12.8.0.0^3,^1^2.0^4,^9.0^1^5,^2^0]docosa-1,3(12),4,6,8,10,13,15,17,19,21-undecaen-7-yl acetate
• IUPAC Traditional name: pentacyclo[12.8.0.0^{3,12}.0^{4,9}.0^{15,20}]docosa-1(14),2,4,6,8,10,12,15,17,19,21-undecaen-7-yl acetate; pentacyclo[12.8.0.0^3,^1^2.0^4,^9.0^1^5,^2^0]docosa-1,3(12),4,6,8,10,13,15,17,19,21-undecaen-7-yl acetate
• Synonyms: 3-Acetoxydibenz[a,h]anthracene; Benzo[k]benz[a]anthracen-3-ol 3-Acetate; Dibenz[a,h]anthracen-3-ol Acetate

Database IDs

• CAS Number: 72378-87-1
• MDL Number: MFCD00269866
• PubChem SID: 162077765
• PubChem CID: 2735227

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 5.538414
• LogD (pH = 7.4): 5.538414
• Log P: 5.538414
• Molar Refractivity: 102.9912 cm^3
• Polarizability: 45.23832 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 247-248°C; 247-248°C

DETAILS

Toronto Research Chemicals - A165000

3-Acetoxydibenz[a,h]anthracene is used in the synthesis of 3-Hydroxydibenz[a,h]anthracene, known to be a metabolite of DBA (Dibenz[a,h]anthracene) (D417010).

REFERENCES

• Lee, H. M., et al.: J. Org. Chem., 47, 5321 (1982)