Structure Database (LMSD)
Common Name
all-trans-retinyl Palmitate
Systematic Name
Synonyms
- (2E,4E,6E,8E)-Hexadecanoic acid 3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2, 4,6,8,tetraenyl ester
3D model of all-trans-retinyl Palmitate
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Retinyl palmitate is a natural ester form of vitamin A .1 It is a major storage form of vitamin A in vivo.2 Retinyl palmitate (1-100 µM) is cytotoxic to HeLa cells both alone and to a greater effect when combined with photodynamic therapy.3 It decreases tumor volume by 50% in a human gallbladder cancer mouse xenograft model when administered at doses of 1,000 or 2,500 IU/animal per day for three weeks and when administered prior to tumor implantation at a dose of 2,500 IU/animal.4
This information has been provided by Cayman Chemical
References
1. McCormick, A.M., and Napoli, J.L. Identification of 5,6-epoxyretinoic acid as an endogenous retinol metabolite. The Journal of Biological Chemisty 257(4), 1730-1735 (1982).
2. O'Byrne, S.M., and Blaner, W.S. Retinol and retinyl esters: Biochemistry and physiology. J. Lipid. Res. 54(7), 1731-1743 (2013).
3. Ibrahim, T., El Rouby, M.N., Al-Sherbini, e.-S.A., et al. Photodecomposition, photomutagenicity and photocytotoxicity of retinyl palmitate under He-Ne laser photoirradiation and its effects on photodynamic therapy of cancer cells <em>in vitro</em>. Photodiagnosis Photodyn.Ther. 13, 316-322 (2016).
String Representations
InChiKey (Click to copy)
VYGQUTWHTHXGQB-FFHKNEKCSA-N
InChi (Click to copy)
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+
SMILES (Click to copy)
C1C(C)(C)C(/C=C/C(=C/C=C/C(=C/COC(CCCCCCCCCCCCCCC)=O)/C)/C)=C(C)CC1
Other Databases
Wikipedia
KEGG ID
HMDB ID
CHEBI ID
LIPIDBANK ID
VVA0008
PubChem CID
SwissLipids ID
Cayman ID
Calculated Physicochemical Properties
Heavy Atoms
38
Rings
1
Aromatic Rings
0
Rotatable Bonds
21
Van der Waals Molecular Volume
620.74
Topological Polar Surface Area
26.30
Hydrogen Bond Donors
0
Hydrogen Bond Acceptors
2
logP
11.83
Molar Refractivity
167.89
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Updated at
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