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MedKoo Cat#: 530210 | Name: ɑ-Tocopherolquinone
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

ɑ-Tocopherolquinone, also known as Vitamin E Quinone (D-form), is a mitochondrial membrane transport protein that has been in phase II clinical trials for the treatment of inherited mitochondrial respiratory chain diseases, however this research has been discontinued. It has also been used for the treatment of Frederich's ataxia and MEILAS syndrome.

Chemical Structure

ɑ-Tocopherolquinone
ɑ-Tocopherolquinone
CAS#7559-04-8

Theoretical Analysis

MedKoo Cat#: 530210

Name: ɑ-Tocopherolquinone

CAS#: 7559-04-8

Chemical Formula: C29H50O3

Exact Mass: 446.3760

Molecular Weight: 446.72

Elemental Analysis: C, 77.97; H, 11.28; O, 10.74

Price and Availability

Size Price Availability Quantity
200mg USD 450.00
500mg USD 950.00
1g USD 1,850.00
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Related CAS #
No Data
Synonym
A-0001; EPI-A-0001; EPIA-0001; A 0001; EPI A 0001; EPIA 000; A 0001; EPI A 0001; EPIA 0001; Vitamin E Quinone (D-form); D-α-Tocopherylquinone, Tocopherylquinone
IUPAC/Chemical Name
ɑ-2-(3-Hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethyl-p-benzoquinone
InChi Key
LTVDFSLWFKLJDQ-UHFFFAOYSA-N
InChi Code
InChI=1S/C29H50O3/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8,32)19-17-26-25(7)27(30)23(5)24(6)28(26)31/h20-22,32H,9-19H2,1-8H3
SMILES Code
O=C(C(C)=C1C)C(C)=C(CCC(C)(O)CCCC(C)CCCC(C)CCCC(C)C)C1=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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 446.72 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.

Recalculate based on batch purity %
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: Opatíková M, Semchonok DA, Kopečný D, Ilík P, Pospíšil P, Ilíková I, Roudnický P, Zeljković SĆ, Tarkowski P, Kyrilis FL, Hamdi F, Kastritis PL, Kouřil R. Cryo-EM structure of a plant photosystem II supercomplex with light- harvesting protein Lhcb8 and α-tocopherol. Nat Plants. 2023 Aug;9(8):1359-1369. doi: 10.1038/s41477-023-01483-0. Epub 2023 Aug 7. PMID: 37550369. 2: Wu DM, Zhang JJ, Guo N, Zheng SJ, Zhu QF, Feng YQ, Peng SS, Wu YH, Tuo MH. Cognitive impairment correlates with serum carbonyl compound profiles in subclinical carotid atherosclerosis. Neuroreport. 2018 Dec 12;29(18):1550-1557. doi: 10.1097/WNR.0000000000001147. PMID: 30325874. 3: Sussmann RAC, Fotoran WL, Kimura EA, Katzin AM. Plasmodium falciparum uses vitamin E to avoid oxidative stress. Parasit Vectors. 2017 Oct 10;10(1):461. doi: 10.1186/s13071-017-2402-3. PMID: 29017543; PMCID: PMC5634829. 4: Huang YP, Liu HX, Song JL, Wu JP, Yuan P, Qiu SX. [Chemical Constituents from Mitrasacme pygmaea]. Zhong Yao Cai. 2016 Feb;39(2):315-7. Chinese. PMID: 30080365. 5: Nowicka B, Kruk J. Plastoquinol is more active than α-tocopherol in singlet oxygen scavenging during high light stress of Chlamydomonas reinhardtii. Biochim Biophys Acta. 2012 Mar;1817(3):389-94. doi: 10.1016/j.bbabio.2011.12.002. Epub 2011 Dec 13. PMID: 22192719. 6: Galli F, Mazzini F, Bamonti L, Gille L, Böhmdorfer S, Piroddi M, Netscher T, Kelly FJ, Rosenau T. Tocotrienamines and tocopheramines: reactions with radicals and metal ions. Bioorg Med Chem. 2011 Nov 1;19(21):6483-91. doi: 10.1016/j.bmc.2011.08.050. Epub 2011 Aug 28. PMID: 21955455. 7: Szymańska R, Kruk J. Gamma-tocopherol dominates in young leaves of runner bean (Phaseolus coccineus) under a variety of growing conditions: the possible functions of gamma-tocopherol. Phytochemistry. 2008 Aug;69(11):2142-8. doi: 10.1016/j.phytochem.2008.05.008. Epub 2008 Jun 24. PMID: 18582912. 8: Kobayashi N, DellaPenna D. Tocopherol metabolism, oxidation and recycling under high light stress in Arabidopsis. Plant J. 2008 Aug;55(4):607-18. doi: 10.1111/j.1365-313X.2008.03539.x. Epub 2008 Apr 30. PMID: 18452591. 9: Kruk J, Trebst A. Plastoquinol as a singlet oxygen scavenger in photosystem II. Biochim Biophys Acta. 2008 Feb;1777(2):154-62. doi: 10.1016/j.bbabio.2007.10.008. Epub 2007 Oct 25. PMID: 18005659. 10: Crisostomo AG, Moreno RB, Navaratnam S, Wilkinson JA, Bisby RH. Generation of superoxide and singlet oxygen from alpha-tocopherolquinone and analogues. Free Radic Res. 2007 Jun;41(6):730-7. doi: 10.1080/10715760701324075. PMID: 17516246; PMCID: PMC2080821. 11: Pazos M, Sánchez L, Medina I. Alpha-tocopherol oxidation in fish muscle during chilling and frozen storage. J Agric Food Chem. 2005 May 18;53(10):4000-5. doi: 10.1021/jf047843k. PMID: 15884830. 12: Pollok D, Melchert HU. Determination of alpha-tocopherolquinone in human serum samples by liquid chromatography with fluorescence detection and on-line post-column derivatization. J Chromatogr A. 2004 Nov 12;1056(1-2):257-62. PMID: 15595560. 13: Kruk J, Jemioła-Rzemińska M, Burda K, Schmid GH, Strzałka K. Scavenging of superoxide generated in photosystem I by plastoquinol and other prenyllipids in thylakoid membranes. Biochemistry. 2003 Jul 22;42(28):8501-5. doi: 10.1021/bi034036q. PMID: 12859196. 14: Shinozaki K, Takeda H, Inazu M, Matsumiya T, Takasaki M. Abnormal incorporation and utilization of alpha-tocopherol in erythrocyte membranes of streptozotocin-induced diabetic rats. Eur J Pharmacol. 2002 Dec 5;456(1-3):133-9. doi: 10.1016/s0014-2999(02)02618-3. PMID: 12450579. 15: Takasaki M, Yanagawa K, Shinozaki K, Fujii H, Shibuya T, Takeda H, Matsumiya T, Egashira T. [Relationship between aging and vitamin E]. Nihon Ronen Igakkai Zasshi. 2002 Sep;39(5):494-500. Japanese. doi: 10.3143/geriatrics.39.494. PMID: 12404740. 16: Carbonaro M, Mattera M, Nicoli S, Bergamo P, Cappelloni M. Modulation of antioxidant compounds in organic vs conventional fruit (peach, Prunus persica L., and pear, Pyrus communis L.). J Agric Food Chem. 2002 Sep 11;50(19):5458-62. doi: 10.1021/jf0202584. PMID: 12207491. 17: Mottier P, Gremaud E, Guy PA, Turesky RJ. Comparison of gas chromatography- mass spectrometry and liquid chromatography-tandem mass spectrometry methods to quantify alpha-tocopherol and alpha-tocopherolquinone levels in human plasma. Anal Biochem. 2002 Feb 1;301(1):128-35. doi: 10.1006/abio.2001.5486. PMID: 11811977. 18: Verleyen T, Kamal-Eldin A, Dobarganes C, Verhe R, Dewettinck K, Huyghebaert A. Modeling of alpha-tocopherol loss and oxidation products formed during thermoxidation in triolein and tripalmitin mixtures. Lipids. 2001 Jul;36(7):719-26. doi: 10.1007/s11745-001-0777-6. PMID: 11521970. 19: Yanagawa K, Takeda H, Egashira T, Matsumiya T, Shibuya T, Takasaki M. Changes in antioxidative mechanisms in elderly patients with non-insulin- dependent diabetes mellitus. Investigation of the redox dynamics of alpha- tocopherol in erythrocyte membranes. Gerontology. 2001 May-Jun;47(3):150-7. doi: 10.1159/000052789. PMID: 11340321. 20: Verleyen T, Verhe R, Huyghebaert A, Dewettinck K, De Greyt W. Identification of alpha-tocopherol oxidation products in triolein at elevated temperatures. J Agric Food Chem. 2001 Mar;49(3):1508-11. doi: 10.1021/jf001142f. PMID: 11312887.