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D-α-Tocopherylquinone

CAT: 0804-HY-N2853-02Size: 10 mM - 1 mLDry Ice: NoHazardous: No
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CAT#:0804-HY-N2853-02Size:10 mM - 1 mL
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Description
D-α-Tocopherylquinone (α-Tocopherylquinone) is a quinone, can be isolated from Phaeodactylum tricornutum. D-α-Tocopherylquinone is an oxidation product of α-Tocopherol (vitamin E) . D-α-Tocopherylquinone can act as an anticoagulant and as an antioxidant. D-α-Tocopherylquinone reduces cellular oxidative damage produced by oxidized lipids. D-α-Tocopherylquinone binds to a liver cytosolic protein with a molecular mass of about 40 kDa. D-α-Tocopherylquinone binds to glurathione-S-transferase (GST) and can be transported to the site of metabolism or excreted in the bile[1][2][3].
CAS Number
7559-04-8
Product Name Alternative
α-Tocopherylquinone
UNSPSC
12352211
Hazard Statement
H302-H315-H319-H335
Target
Reactive Oxygen Species (ROS)
Type
Natural Products
Related Pathways
Immunology/Inflammation; Metabolic Enzyme/Protease; NF-κB
Applications
Cancer-programmed cell death
Field of Research
Others
Assay Protocol
https://www.medchemexpress.com/d-α-tocopherylquinone.html
Concentration
10mM
Purity
98.92
Solubility
DMSO : 50 mg/mL (ultrasonic; warming; heat to 60°C)
Smiles
CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@@](C)(O)CCC1=C(C(C(C)=C(C)C1=O)=O)C
Molecular Formula
C29H50O3
Molecular Weight
446.71
Precautions
P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501
References & Citations
[1]K Shimazaki, et al. Studies on electron transfer systems in the marine diatom Phaeodactylum tricornutum. II. Identification and determination of quinones, cytochromes, and flavins. J Biochem. 1978 Jun;83 (6) :1639-42.|[2]M K Horwitt. Vitamin E: a reexamination. Am J Clin Nutr. 1976 May;29 (5) :569-78.|[3]Arita, M., et al., (1998) . Binding of alpha-tocopherylquinone, an oxidized form of alpha-tocopherol, to glutathione-S-transferase in the liver cytosol. FEBS letters, 436 (3), 424–426.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Tocopherol quinone

alpha-tocopherylquinone has been reported in Pourthiaea arguta, Garcinia multiflora, and other organisms with data available.

CAS Number7559-04-8
PubChem CID2734086
IUPAC Name2-[(3R,7R,11R)-3-hydroxy-3,7,11,15-tetramethylhexadecyl]-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione
Molecular FormulaC29H50O3
Molecular Weight446.7
XLogP8.8
Topological Polar Surface Area54.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count15
Heavy Atom Count32
Formal Charge0
Complexity697
SMILES
CC1=C(C(=O)C(=C(C1=O)C)CC[C@@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)C)O)C
InChI
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/t21-,22-,29-/m1/s1
InChIKey
LTVDFSLWFKLJDQ-IEOSBIPESA-N
Chemical Structure
2D Structure
2D structure of Tocopherol quinone
CAS: 7559-04-8
CID: 2734086
Formula: C29H50O3
MW: 446.7
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight446.7
XLogP38.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count15
Exact Mass446.37599545
Monoisotopic Mass446.37599545
Topological Polar Surface Area54.4 Ų
Heavy Atom Count32
Formal Charge0
Complexity697
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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