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Technical details about MolPort-002-070-540, learn more about the structure, uses, toxicity, action, side effects and more

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2D Structure
1. Also known as: 83-32-9, 1,2-dihydroacenaphthylene, 1,8-ethylenenaphthalene, Peri-ethylenenaphthalene, Naphthyleneethylene, Acenaphthylene, 1,2-dihydro-
Molecular Formula
C12H10
Molecular Weight
154.21  g/mol
InChI Key
CWRYPZZKDGJXCA-UHFFFAOYSA-N
FDA UNII
V8UT1GAC5Y

acenaphthene is a natural product found in Salvia coccinea and Gossypium hirsutum with data available.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1,2-dihydroacenaphthylene
2.1.2 InChI
InChI=1S/C12H10/c1-3-9-4-2-6-11-8-7-10(5-1)12(9)11/h1-6H,7-8H2
2.1.3 InChI Key
CWRYPZZKDGJXCA-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1CC2=CC=CC3=C2C1=CC=C3
2.2 Other Identifiers
2.2.1 UNII
V8UT1GAC5Y
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 83-32-9

2. 1,2-dihydroacenaphthylene

3. 1,8-ethylenenaphthalene

4. Peri-ethylenenaphthalene

5. Naphthyleneethylene

6. Acenaphthylene, 1,2-dihydro-

7. Ethylenenaphthalene

8. 1,8-dihydroacenaphthalene

9. V8ut1gac5y

10. Chebi:22154

11. Nsc-7657

12. Mfcd00003807

13. Dsstox_cid_1774

14. Dsstox_rid_76319

15. Dsstox_gsid_21774

16. Cas-83-32-9

17. Ccris 5951

18. Hsdb 2659

19. Nsc 7657

20. Einecs 201-469-6

21. Unii-v8ut1gac5y

22. 1,2-dihydro Acenaphthylene

23. Ai3-00128

24. Acenaphthene, 97%

25. Acenaphthene, 99%

26. Acenaphthene,

27. Acenaphthene [mi]

28. Acenaphthene [hsdb]

29. Acenaphthene [iarc]

30. Ec 201-469-6

31. Naphthalene, 1,8-ethylene-

32. Bidd:gt0787

33. Chembl1797271

34. Dtxsid3021774

35. Acenaphthene, Analytical Standard

36. Nsc7657

37. Zinc1235986

38. Tox21_202400

39. Tox21_300013

40. Stl483068

41. Akos000119983

42. Fs-4341

43. Acenaphthene 100 Microg/ml In Methanol

44. Ncgc00163966-01

45. Ncgc00163966-02

46. Ncgc00163966-03

47. Ncgc00163966-04

48. Ncgc00254079-01

49. Ncgc00259949-01

50. Ac-19767

51. Acenaphthene 10 Microg/ml In Acetonitrile

52. Acenaphthene 100 Microg/ml In Acetonitrile

53. Db-056708

54. A0003

55. A0135

56. Acenaphthene 1000 Microg/ml In Acetonitrile

57. Ft-0621716

58. C19312

59. D97698

60. Acenaphthene Zone Refined (number Of Passes:30)

61. Q415103

62. W-104147

63. Z56926550

64. 73bcd470-1e93-4e76-bf03-e06fb8fe00ea

65. Acenaphthene, Certified Reference Material, Tracecert(r)

66. F1908-0103

67. Acenaphthene Solution, 100 Mug/ml In Cyclohexane, Analytical Standard

68. Acenaphthene Solution, Certified Reference Material, 200 Mug/ml In Methanol

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 154.21 g/mol
Molecular Formula C12H10
XLogP33.9
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count0
Rotatable Bond Count0
Exact Mass154.078250319 g/mol
Monoisotopic Mass154.078250319 g/mol
Topological Polar Surface Area0 Ų
Heavy Atom Count12
Formal Charge0
Complexity155
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 Absorption, Distribution and Excretion

The waxy surface of some plant leaves and fruits can concentrate polyaromatic hydrocarbons through surface adsorption. /Polynuclear aromatic hydrocarbons/

USEPA; Ambient Water Quality Criteria Doc: Polynuclear Aromatic Hydrocarbons p.C-11 (1980)


4.2 Metabolism/Metabolites

The filamentous fungus Cunninghamella elegans ATCC 36112 metabolized within 72 hr of incubation approximately 64% of the [1,8-(14)C]acenaphthene added. The radioactive metabolites were extracted with ethyl acetate and separated by thin-layer chromatography and reversed-phase high-performance liquid chromatography. Seven metabolites were identified by 1H nuclear magnetic resonance, UV, and mass spectral techniques as 6-hydroxyacenaphthenone (24.8%), 1,2-acenaphthenedione (19.9%), trans-1,2-dihydroxyacenaphthene (10.3%), 1,5-dihydroxyacenaphthene (2.7%), 1-acenaphthenol (2.4%), 1-acenaphthenone (2.1%), and cis-1,2-dihydroxyacenaphthene (1.8%). Parallel experiments with rat liver microsomes indicated that the major metabolite formed from acenaphthene by rat liver microsomes was 1-acenaphthenone. The fungal metabolism of acenaphthene was similar to bacterial and mammalian metabolism, since the primary site of enzymatic attack was on the two carbons of the five-member ring.

PMID:1482186 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC183157 Pothuluri JV et al; Appl Environ Microbiol 58 (11): 3654-9 (1992)


Metabolized to naphthalene-1,8-dicarboxylic acid in rats. /From table/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. A-1


... Possibility of limited metabolism of acenaphthene to naphthalic acid and naphthalic anhydride.

Acenaphthene; pp 46-7 in Priority Toxic Pollutants; Sittig M, ED (1980)


A Beijerinckia species and a mutant strain, Beijerinckia species strain B8/36, were shown to oxidize the polycyclic aromatic hydrocarbons acenaphthene and acenaphthylene. Both organisms oxidized acenaphthene to the same spectrum of metabolites, which included 1-acenaphthenol, 1-acenaphtheneone, 1,2-acenaphthenediol, acenaphthenequinone, and a compound that was tentatively identified as 1,2-dihydroxyacenaphthylene. In contrast, acenaphthylene was oxidized to acenaphthenequinone and the compound tentatively identified as 1,2-dihydroxyacenaphthylene was also formed when the organism was incubated with synthetic cis-1,2-acenaphthenediol. A metabolite identified as cis-1,2-acenaphthenediol was formed from acenaphthylene by the mutant Beijerinckia species strain B8/36. Cell extracts prepared from the wild-type Beijerinckia strain contain a constitutive pyridine nucleotide-dependent dehydrogenase which can oxidize 1-acenaphthenol and 9-fluorenol. The results indicate that although acenaphthene and acenaphthylene are both oxidized to acenaphthenequinone, the pathways leading to the formation of this end product are different.

PMID:6089663 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC240288 Schocken MJ, Gibson DT; Appl Environ Microbiol 48 (1): 10-16 (1984)


For more Metabolism/Metabolites (Complete) data for ACENAPHTHENE (7 total), please visit the HSDB record page.


4.3 Biological Half-Life

The half-life of acenaphthene in /the bluegill fish/ is less than 1 day.

USEPA; Ambient Water Quality Criteria Doc: Acenaphthene (Draft) p.B-2 (1980)


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