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Chemistry

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Also known as: 514-78-3, Orobronze, Carophyll red, Beta,beta-carotene-4,4'-dione, Food orange 8, Cantaxanthin

Molecular Formula

C₄₀H₅₂O₂

Molecular Weight

564.8 g/mol

InChI Key

FDSDTBUPSURDBL-DKLMTRRASA-N

FDA UNII

4C3C6403MU

A trans-carotenoid pigment widely distributed in nature. The compound is used as an oral suntanning agent and as a food and drug coloring agent. Oral ingestion of the compound causes canthaxanthin retinopathy.

1 2D Structure

Canthaxanthin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2,4,4-trimethyl-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethyl-3-oxocyclohexen-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]cyclohex-2-en-1-one

2.1.2 InChI

InChI=1S/C40H52O2/c1-29(17-13-19-31(3)21-23-35-33(5)37(41)25-27-39(35,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-36-34(6)38(42)26-28-40(36,9)10/h11-24H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+

2.1.3 InChI Key

FDSDTBUPSURDBL-DKLMTRRASA-N

2.1.4 Canonical SMILES

CC1=C(C(CCC1=O)(C)C)C=CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC2=C(C(=O)CCC2(C)C)C)C)C

2.1.5 Isomeric SMILES

CC1=C(C(CCC1=O)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C2=C(C(=O)CCC2(C)C)C)\C)\C)/C)/C

2.2 Other Identifiers

2.2.1 UNII

4C3C6403MU

2.3 Synonyms

2.3.1 MeSH Synonyms

1. C.i. 40850

2. Canthaxanthine

3. Carophyll Red

4. Food Orange 8

5. Orobronze

6. Roxanthin Red 10

2.3.2 Depositor-Supplied Synonyms

1. 514-78-3

2. Orobronze

3. Carophyll Red

4. Beta,beta-carotene-4,4'-dione

5. Food Orange 8

6. Cantaxanthin

7. Canthaxanthine

8. Roxanthin Red 10

9. Cantaxanthine

10. L-orange 7

11. 4,4'-dioxo-beta-carotene

12. Canthaxanthin (trans)

13. Canthaxanthin, Powder

14. Ci 40850

15. All-trans,beta-carotene-4,4'-dione

16. Chebi:3362

17. 4c3c6403mu

18. Nsc-374110

19. Ncgc00095896-01

20. 2,4,4-trimethyl-3-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-3,7,12,16-tetramethyl-18-(2,6,6-trimethyl-3-oxocyclohexen-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]cyclohex-2-en-1-one

21. C.i. Food Orange 8

22. All-trans-canthaxanthin

23. 3,3'-((1e,3e,5e,7e,9e,11e,13e,15e,17e)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaene-1,18-diyl)bis(2,4,4-trimethylcyclohex-2-en-1-one)

24. Carotene-4,4'-dione, Beta-

25. Ccris 3276

26. E 161g

27. Einecs 208-187-2

28. Nsc 374110

29. Ro 1-9915

30. E 161 G

31. Brn 1898520

32. Beta-carotene-4,4'-dione, All-trans-

33. Unii-4c3c6403mu

34. Canthaxanthin (euglenanone)

35. Mfcd00016364

36. Cantha

37. Kantakisantin

38. Canthaxanthin, Tech.

39. Lucantin Red

40. Isomer Of Canthaxanthin

41. 4,4'-diketo-b-carotene

42. Ci-food Orange 8

43. Dsstox_cid_2727

44. Canthaxanthin [mi]

45. Beta-carotin-4,4?-dione

46. Canthaxanthin [fcc]

47. 4,4'-diketo-beta-carotene

48. Dsstox_rid_76702

49. Dsstox_gsid_22727

50. Schembl19618

51. 4-07-00-02680 (beilstein Handbook Reference)

52. Canthaxanthin [mart.]

53. E161g

54. Ins No.161g

55. Spectrum1504204

56. Canthaxanthin [who-dd]

57. Ins-161g

58. Chembl1329004

59. Dtxsid0022727

60. Schembl12920083

61. Canthaxanthin (e 161g)

62. Ci 40850 [inci]

63. Hms2089k15

64. Hy-b1960

65. Tox21_111533

66. All-trans-beta-carotene-4,4'-dione

67. Canthaxanthin, >=95.0% (hplc)

68. E-161g

69. Lmpr01070264

70. Nsc374110

71. Zinc17653971

72. .beta.-carotene-4,4'-dione

73. 4,4'-diketo-.beta.-carotene

74. Ccg-207976

75. Cs-6879

76. Cas-514-78-3

77. Ls-15425

78. Ro-19915

79. Canthaxanthin (trans), Analytical Standard

80. Canthaxanthine 10 Microg/ml In Acetonitrile

81. Ci-(1975)no.40850

82. C08583

83. Ab00053349-02

84. Q385657

85. W-105885

86. Canthaxanthine. Short Expiry Date Due To Chemical Nature Of Component(s)

87. 3,3'-((1e,3e,5e,7e,9e,11e,13e,15e,17e)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaene-1,18-diyl)bis(2,4,4-trimethylcyclohex-2-enone)

2.4 Create Date

2005-03-27

3 Chemical and Physical Properties

Molecular Formula	C₄₀H₅₂O₂
Molecular Weight	564.8 g/mol
XLogP3	11.4
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	10
Exact Mass	564.396730897 g/mol
Monoisotopic Mass	564.396730897 g/mol
Topological Polar Surface Area	34.1 Å²
Heavy Atom Count	42
Formal Charge	0
Complexity	1270
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	9
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Antioxidants

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)

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