WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 414885
CAS#: 17407-37-3 (Hemisuccinate)
Description: Vitamin E Succinate, also known as D –α-Tocopherol Hemisuccinate is a weakly acidic derivative of D –α-Tocopherol Hemisuccinate. It acts as an ionizable anionic surfactant and is commonly used to stabilize PE-rich pH-sensitive liposomes. It has been used as a precursor of D –α-Tocopherol for the protection of liver toxicity in an animal model. It was also reported that alpha-tocopheryl succinate has in vivo anti-tumour activity, due to induce apoptosis by causing lysosomal instability.
MedKoo Cat#: 414885
Name: Vitamin E Succinate
CAS#: 17407-37-3 (Hemisuccinate)
Related CAS #: 59-02-9 (vitamin E) 58-95-7 (acetate) 17407-37-3 (Hemisuccinate) 9002-96-4 (PEG 1000 succinate)
Synonym: D –α-Tocopherol Hemisuccinate; Vitamin E Succinate; Tocopherol succinate;
IUPAC/Chemical Name: 4-oxo-4-[[2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydrochromen-6-yl]oxy]butanoic acid
InChi Key: IELOKBJPULMYRW-UHFFFAOYSA-N
InChi Code: InChI=1S/C33H54O5/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-20-33(8)21-19-28-27(7)31(25(5)26(6)32(28)38-33)37-30(36)18-17-29(34)35/h22-24H,9-21H2,1-8H3,(H,34,35)
SMILES Code: O=C(O)CCC(OC1=C(C)C(CCC(CCCC(C)CCCC(C)CCCC(C)C)(C)O2)=C2C(C)=C1C)=O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
|Concentration / Solvent Volume / Mass||1 mg||5 mg||10 mg|
|1 mM||1.15 mL||5.76 mL||11.51 mL|
|5 mM||0.23 mL||1.15 mL||2.3 mL|
|10 mM||0.12 mL||0.58 mL||1.15 mL|
|50 mM||0.02 mL||0.12 mL||0.23 mL|
1: Xu H, Deng YH, Wang KQ, Chen DW. Preparation and characterization of stable pH-sensitive vesicles composed of α-tocopherol hemisuccinate. AAPS PharmSciTech. 2012 Dec;13(4):1377-85. doi: 10.1208/s12249-012-9863-7. Epub 2012 Oct 3. PMID: 23054989; PMCID: PMC3513435.
2: Huang C, Chen F, Zhang L, Yang Y, Yang X, Pan W. 99mTc Radiolabeled HA/TPGS-Based Curcumin-Loaded Nanoparticle for Breast Cancer Synergistic Theranostics: Design, in vitro and in vivo Evaluation. Int J Nanomedicine. 2020 Apr 30;15:2987-2998. doi: 10.2147/IJN.S242490. PMID: 32431497; PMCID: PMC7200226.
3: Quiñones JP, Mardare CC, Hassel AW, Brüggemann O. Testosterone- and vitamin- grafted cellulose ethers for sustained release of camptothecin. Carbohydr Polym. 2019 Feb 15;206:641-652. doi: 10.1016/j.carbpol.2018.11.047. Epub 2018 Nov 19. Erratum in: Carbohydr Polym. 2019 Mar 15;208:323-327. PMID: 30553368.
4: Ivanova AN, Belsky YP, Spivak AY, Danilets MG, Belska NV, Chalitova RR, Ligatcheva AA, Uchasova EG. In vitro effect of combined hybrid molecules from vitamin E analogues and betulinic acid on macrophage activity. Bull Exp Biol Med. 2011 Oct;151(6):694-7. doi: 10.1007/s10517-011-1418-5. PMID: 22485210.
5: Torres E, Mainini F, Napolitano R, Fedeli F, Cavalli R, Aime S, Terreno E. Improved paramagnetic liposomes for MRI visualization of pH triggered release. J Control Release. 2011 Sep 5;154(2):196-202. doi: 10.1016/j.jconrel.2011.05.017. Epub 2011 May 20. PMID: 21621569.
6: Lai MZ, Düzgüneş N, Szoka FC. Effects of replacement of the hydroxyl group of cholesterol and tocopherol on the thermotropic behavior of phospholipid membranes. Biochemistry. 1985 Mar 26;24(7):1646-53. doi: 10.1021/bi00328a012. PMID: 3839132.
7: Tirmenstein MA, Leraas TL, Fariss MW. alpha-Tocopheryl hemisuccinate administration increases rat liver subcellular alpha-tocopherol levels and protects against carbon tetrachloride-induced hepatotoxicity. Toxicol Lett. 1997 Jun 16;92(1):67-77. doi: 10.1016/s0378-4274(97)00036-2. PMID: 9242359.
8: Janoff AS, Kurtz CL, Jablonski RL, Minchey SR, Boni LT, Gruner SM, Cullis PR, Mayer LD, Hope MJ. Characterization of cholesterol hemisuccinate and alpha- tocopherol hemisuccinate vesicles. Biochim Biophys Acta. 1988 Jun 22;941(2):165-75. doi: 10.1016/0005-2736(88)90177-0. PMID: 2838079.
9: Tirmenstein MA, Ge X, Elkins CR, Fariss MW. Administration of the tris salt of alpha-tocopheryl hemisuccinate inactivates CYP2E1, enhances microsomal alpha- tocopherol levels and protects against carbon tetrachloride-induced hepatotoxicity. Free Radic Biol Med. 1999 Apr;26(7-8):825-35. doi: 10.1016/s0891-5849(98)00265-2. PMID: 10232825.
10: Bradford A, Atkinson J, Fuller N, Rand RP. The effect of vitamin E on the structure of membrane lipid assemblies. J Lipid Res. 2003 Oct;44(10):1940-5. doi: 10.1194/jlr.M300146-JLR200. Epub 2003 Jul 16. PMID: 12867540.
[Hiroaki Jizomoto *, Eri Kanaoka, Koichiro Hirano, pH-Sensitive liposomes composed of tocopherol hemisuccinate and of phosphatidylethanolamine including tocopherol hemisuccinate. Biochimica et Biophysics Acta 1213 (1994) 343-348]
[Tirmenstein, M.A., Leraas, T.L., Fariss, M.W., 1997. alpha-Tocopheryl hemisuccinate administration increases rat liver subcellular alpha-tocopherol levels and protects against carbon tetrachloride-induced hepatotoxicity. Toxicol. Lett. 92, 67–77]
. [Neuzil J, Zhao M, Ostermann G, Sticha M, Gellert N, Weber C, et al. Alpha-tocopheryl succinate, an agent with in vivo anti-tumour activity, induces apoptosis by causing lysosomal instability. Biochem J 2002; 362 (Pt 3):709–715]