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2D Structure
Also known as: Retinyl palmitate, 79-81-2, Retinol palmitate, Retinol, hexadecanoate, All-trans-retinyl palmitate, Arovit
Molecular Formula
C36H60O2
Molecular Weight
524.9  g/mol
InChI Key
VYGQUTWHTHXGQB-FFHKNEKCSA-N
FDA UNII
1D1K0N0VVC

Retinyl Palmitate is a naturally-occurring phenyl analogue of retinol (vitamin A) with potential antineoplastic and chemopreventive activities. As the most common form of vitamin A taken for dietary supplementation, retinyl palmitate binds to and activates retinoid receptors, thereby inducing cell differentiation and decreasing cell proliferation. This agent also inhibits carcinogen-induced neoplastic transformation, induces apoptosis in some cancer cell types, and exhibits immunomodulatory properties. (NCI04)
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl] hexadecanoate
2.1.2 InChI
InChI=1S/C36H60O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-25-35(37)38-30-28-32(3)23-20-22-31(2)26-27-34-33(4)24-21-29-36(34,5)6/h20,22-23,26-28H,7-19,21,24-25,29-30H2,1-6H3/b23-20+,27-26+,31-22+,32-28+
2.1.3 InChI Key
VYGQUTWHTHXGQB-FFHKNEKCSA-N
2.1.4 Canonical SMILES
CCCCCCCCCCCCCCCC(=O)OCC=C(C)C=CC=C(C)C=CC1=C(CCCC1(C)C)C
2.1.5 Isomeric SMILES
CCCCCCCCCCCCCCCC(=O)OC/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(CCCC1(C)C)C
2.2 Other Identifiers
2.2.1 UNII
1D1K0N0VVC
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Chocola A

2. Retinol Palmitate

3. Retinyl Palmitate

2.3.2 Depositor-Supplied Synonyms

1. Retinyl Palmitate

2. 79-81-2

3. Retinol Palmitate

4. Retinol, Hexadecanoate

5. All-trans-retinyl Palmitate

6. Arovit

7. Optovit-a

8. Retinyl Hexadecanoate

9. Aquapalm

10. Dispatabs Tabs

11. Vitazyme A

12. Optovit A

13. Axerophthol Palmitate

14. Trans-retinol Palmitate

15. Trans-retinyl Palmitate

16. [(2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl] Hexadecanoate

17. Lutavit A 500 Plus

18. All-trans-retinol Palmitate

19. Arovit (roche)

20. All-trans-vitamin A Palmitate

21. Aquasol A (tn)

22. Retinyl (vitamin A) Palmitate

23. Retinol Palmitate [jan]

24. O~15~-hexadecanoylretinol

25. Nsc-758478

26. 1d1k0n0vvc

27. Retinol, Palmitate, All-trans

28. Ester Found In Fish Liver Oils

29. Retinol Palmitate (6ci,7ci)

30. Chebi:17616

31. Palmitic Acid, Ester With Retinol

32. Retinol, Palmitate, All-trans- (8ci)

33. Ncgc00095056-03

34. Dsstox_cid_1241

35. Dsstox_rid_76033

36. Dsstox_gsid_21241

37. (2e,4e,6e,8e)-hexadecanoic Acid 3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2, 4,6,8,tetraenyl Ester

38. Vitamin A Solubilized

39. Cas-79-81-2

40. (2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl Hexadecanoate

41. Smr000112463

42. Ccris 3280

43. Retinol, Palmitate, All-trans-

44. Einecs 201-228-5

45. Unii-1d1k0n0vvc

46. Brn 1917366

47. Retinylpalmitate

48. Retinol-palmitate

49. Retinyl-palmitate

50. Retinol, All-trans-, Palmitate

51. Palmitic Acid Retinol

52. Retinyl Palmitic Acid

53. Vitamin- A Palmitate

54. Retinyl Hexadecanoic Acid

55. Spectrum5_001201

56. All-(e)-retinol Palmitate

57. Bmse000501

58. Ec 201-228-5

59. Retinol Palmitate (jp17)

60. Chembl1675

61. Schembl41649

62. Mls001332437

63. Mls001332438

64. Spectrum1503604

65. All-trans-retinyl Hexadecanoate

66. Dtxsid1021241

67. Retinyl Palmitate [inci]

68. Hms500m11

69. Retinyl Palmitate [vandf]

70. Vitamin A Palmitate [mi]

71. Hms1922e10

72. Hms2093g13

73. Hms2268c06

74. Pharmakon1600-01503604

75. Retinol Palmitate [who-dd]

76. Retinyl Palmitate [usp-rs]

77. (2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl Palmitate

78. Amy13840

79. Hy-b1384

80. Vae 16:0

81. Vitamin A Palmitate [vandf]

82. Zinc8214494

83. Tox21_113452

84. Tox21_303008

85. Ccg-39342

86. Lmpr01090013

87. Mfcd00019414

88. Nsc758478

89. S4126

90. Retinol, O~15~-(1-oxohexadecyl)-

91. Akos015918435

92. Nsc 758478

93. Vitamin A Palmitate, 1.7 M.i.u./g

94. Idi1_000249

95. Ncgc00095056-01

96. Ncgc00095056-02

97. Ncgc00256427-01

98. Ac-20001

99. Vitamin A Palmitate [orange Book]

100. Sbi-0051830.p002

101. All-(e)-retinol Palmitate [who-ip]

102. Cs-0013116

103. C02588

104. C76552

105. D00164

106. Ab00052360_04

107. A839762

108. Sr-05000001910

109. Vitamin A Palmitate (solubilized) [vandf]

110. Q7316807

111. Sr-05000001910-1

112. Retinyl Palmitate (vitamin A Palmitate; Retinol Palmitate)

113. Retinyl Palmitate, Potency: >=1,700,000 Usp Units Per G

114. Vitamin A (as Palmitate & Beta Carotene) [vandf]

115. Retinyl Palmitate, Type Iv, ~1,800,000 Usp Units/g, Oil

116. Retinyl Palmitate, United States Pharmacopeia (usp) Reference Standard

117. [3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl] Hexadecanoate

118. 3,7-dimethyl-9-(2,6,6,-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol Palmitate

119. (2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-en-1-yl)-2,4,6,8-nonateetraen-1-yl-palmitate

120. (2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenyl Palmitate

121. 110067-62-4

122. Hexadecanoic Acid [(2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenyl] Ester

123. Retinyl Palmitate (vitamin A Palmitate), Pharmaceutical Secondary Standard; Certified Reference Material

124. Retinyl Palmitate Solution, 100 Mug/ml (ethanol With 0.1% (w/v) Bht), Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 524.9 g/mol
Molecular Formula C36H60O2
XLogP313.6
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count21
Exact Mass524.45933115 g/mol
Monoisotopic Mass524.45933115 g/mol
Topological Polar Surface Area26.3 Ų
Heavy Atom Count38
Formal Charge0
Complexity803
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count4
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Anticarcinogenic Agents

Agents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved. (See all compounds classified as Anticarcinogenic Agents.)


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.)