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Lutein

Synopsis

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Chemistry

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Also known as: Xanthophyll, 127-40-2, Bo-xan, Vegetable lutein, Vegetable luteol, All-trans-lutein

Molecular Formula

C₄₀H₅₆O₂

Molecular Weight

568.9 g/mol

InChI Key

KBPHJBAIARWVSC-RGZFRNHPSA-N

FDA UNII

X72A60C9MT

Lutein

A xanthophyll found in the major LIGHT-HARVESTING PROTEIN COMPLEXES of plants. Dietary lutein accumulates in the MACULA LUTEA.

1 2D Structure

Lutein

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-3,5,5-trimethylcyclohex-3-en-1-ol

2.1.2 InChI

InChI=1S/C40H56O2/c1-29(17-13-19-31(3)21-23-37-33(5)25-35(41)27-39(37,7)8)15-11-12-16-30(2)18-14-20-32(4)22-24-38-34(6)26-36(42)28-40(38,9)10/h11-25,35-37,41-42H,26-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t35-,36+,37-/m0/s1

2.1.3 InChI Key

KBPHJBAIARWVSC-RGZFRNHPSA-N

2.1.4 Canonical SMILES

CC1=C(C(CC(C1)O)(C)C)C=CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC2C(=CC(CC2(C)C)O)C)C)C

2.1.5 Isomeric SMILES

CC1=C(C(C[C@@H](C1)O)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/[C@H]2C(=C[C@@H](CC2(C)C)O)C)/C)/C

2.2 Other Identifiers

2.2.1 UNII

X72A60C9MT

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Beta,epsilon-carotene-3, 3'-diol, (3r,3'r,6's)-

2. Beta,epsilon-carotene-3,3'-diol, (3s,3'r,6's)-

3. Gamma Lutein

4. Lutein F

5. Lutein G

6. Lutein, Gamma

2.3.2 Depositor-Supplied Synonyms

1. Xanthophyll

2. 127-40-2

3. Bo-xan

4. Vegetable Lutein

5. Vegetable Luteol

6. All-trans-lutein

7. Xantofyl

8. Lutein Ester

9. Lutein A

10. All-trans-(+)-xanthophyll

11. Floraglo

12. Floraglo Lutein

13. Trans-lutein

14. Lutein, All-trans-

15. All-trans-xanthophyll

16. Oro Glo 7

17. E 161b

18. Beta,epsilon-carotene-3,3'-diol, (3r,3'r,6'r)-

19. Xanthophyll, All-trans-(+)-

20. (3r,3'r,6'r)-lutein

21. Beta,epsilon-carotene-3,3'-diol

22. Os 24

23. Lutein From Tagetes Erecta

24. Ins No.161b(i)

25. X72a60c9mt

26. E 161

27. Chebi:28838

28. Ins-161b(i)

29. E-161b

30. E-161b(i)

31. Nsc-59193

32. .beta.,.epsilon.-carotene-3,3'-diol

33. .beta.,.epsilon.-carotene-3,3'-diol, (3r,3'r,6'r)-

34. (1r)-4-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-18-[(1r,4r)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-3,5,5-trimethylcyclohex-3-en-1-ol

35. (1r,4r)-4-((1e,3e,5e,7e,9e,11e,13e,15e,17e)-18-((r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl)-3,5,5-trimethylcyclohex-2-enol

36. (3r,3'r,6'r)-beta,epsilon-carotene-3,3'-diol

37. 180580-60-3

38. 9-cis-lutein

39. Lutamax

40. 13-cis-lutein

41. Unii-x72a60c9mt

42. Leutein

43. Ncgc00167965-01

44. 15-cis-lutein

45. Einecs 204-840-0

46. 13'-cis-lutein

47. Nsc 59193

48. Lutein (xanthophyll)

49. (9'z)-lutein

50. Lutein - 5%

51. Leutein [vandf]

52. Xanthophyll (~80%)

53. Lutein [vandf]

54. E-carotene-3,3'-diol

55. Lutein - 10%

56. Lutein - 20%

57. Lutein [dsc]

58. Lutein [fcc]

59. Xanthophyll [mi]

60. Lutein [usp-rs]

61. Lutein [mart.]

62. Xanthophyll, From Marigold

63. Xantofyl [who-dd]

64. Lutein, Analytical Standard

65. Dsstox_cid_26749

66. Dsstox_rid_81874

67. Dsstox_gsid_46749

68. Schembl19342

69. 3,3'-dihydroxy-alpha-carotene

70. Chembl173929

71. Dtxsid8046749

72. (invertedexclamationmarka)-lutein

73. Bcbcmap01_000190

74. Hms3886i13

75. 29414-89-9

76. Hy-n6947

77. Zinc8221225

78. (3r,3'r)-dihydroxy-alpha-carotene

79. Tox21_112594

80. ( Inverted Exclamation Marka)-lutein

81. Bbl101804

82. Lmpr01070274

83. Mfcd00017353

84. S5103

85. Stl555601

86. Akos008901394

87. Ccg-270087

88. Db00137

89. Smp1_000317

90. As-63011

91. Cas-127-40-2

92. Xl176941

93. Xl176947

94. Xl176948

95. Cs-0015250

96. C08601

97. Q63409232

98. Lutein Solution, 1 Mg/l In Ethanol, Analytical Standard

99. 4',5'-didehydro-6'-hydro-.beta.-carotene-3,3'-diol #

100. Ab972dac-e626-49f1-898d-598af7729fd0

101. (3r,3'r,6r)-4,5-didehydro-5,6-dihydro-beta,beta-carotene-3,3'-diol

102. Lutein, Pharmaceutical Secondary Standard; Certified Reference Material

103. (3r,3'r,6r)-4,5-didehydro-5,6-dihydro-.beta.,.beta.-carotene-3,3'-diol

104. (3r,3'r,6r)-4,5-didehydro-5,6-dihydro-.beta.,.beta.-carotin-3,3'-diol

105. .beta.,.beta.-carotene-3,3'-diol, 4,5-didehydro-5,6-dihydro-, (3r,3'r,6r)-

106. (1r)-4-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-18-[(1r,4r)-4-hydroxy-2,6,6-trimethyl-cyclohex-2-en-1-yl]-3,7,12,16-tetramethyl-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-3,5,5-trimethyl-cyclohex-3-en-1-ol

107. (1r,4r)-4-((1e,3e,5e,7e,9e,11e,13e,15e,17e)-18-((4r)-4-hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-3,7,12,16-tetramethyl-1,3,5,7,9,11,13,15,17-octadecanonaen-1-yl)-3,5,5-trimethyl-2-cyclohexen-1-ol

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₄₀H₅₆O₂
Molecular Weight	568.9 g/mol
XLogP3	11
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	10
Exact Mass	568.42803102 g/mol
Monoisotopic Mass	568.42803102 g/mol
Topological Polar Surface Area	40.5 Å²
Heavy Atom Count	42
Formal Charge	0
Complexity	1270
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	9
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Xanthophylls are taken for nutritional supplementation, and also for treating dietary shortage or imbalance.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Lutein was found to be present in a concentrated area of the macula, a small area of the retina responsible for central vision. The hypothesis for the natural concentration is that lutein helps protect from oxidative stress and high-energy light. Several studies show that an increase in macula pigmentation decreases the risk for eye diseases such as Age-related Macular Degeneration (AMD).

5.2 Mechanism of Action

Xanthophylls have antioxidant activity and react with active oxygen species, producing biologically active degradation products. They also can inhibit peroxidation of membrane phospholipids and reduce lipofuscin formation, both of which contribute to their antioxidant properties. Lutein is naturally present in the macula of the human retina. It filters out potentially phototoxic blue light and near-ultraviolet radiation from the macula. The protective effect is due in part, to the reactive oxygen species quenching ability of these carotenoids. Lutein is more stable to decomposition by pro-oxidants than are other carotenoids such as beta-carotene and lycopene. Lutein is abundant in the region surrounding the fovea, and lutein is the predominant pigment at the outermost periphery of the macula. Zeaxanthin, which is fully conjugated (lutein is not), may offer somewhat better protection than lutein against phototoxic damage caused by blue and near-ultraviolet light radiation. Lutein is one of only two carotenoids that have been identified in the human lens, may be protective against age-related increases in lens density and cataract formation. Again, the possible protection afforded by lutein may be accounted for, in part, by its reactive oxygen species scavenging abilities. Carotenoids also provide protection from cancer. One of the mechanisms of this is by increasing the expression of the protein connexin-43, thereby stimulating gap junctional communication and preventing unrestrained cell proliferation.

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Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country	Total Quantity (KGS)	Average Price (USD/KGS)	Number of Transactions

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