D9150
2,3-Dimethoxy-5-methyl-p-benzoquinone
apoptosis inducer
Synonym(s):
Coenzyme Q0
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About This Item
Empirical Formula (Hill Notation):
C9H10O4
CAS Number:
Molecular Weight:
182.17
UNSPSC Code:
12352204
NACRES:
NA.51
PubChem Substance ID:
EC Number:
210-100-8
Beilstein/REAXYS Number:
1640422
MDL number:
Product Name
2,3-Dimethoxy-5-methyl-p-benzoquinone, apoptosis inducer
InChI
1S/C9H10O4/c1-5-4-6(10)8(12-2)9(13-3)7(5)11/h4H,1-3H3
SMILES string
COC1=C(OC)C(=O)C(C)=CC1=O
InChI key
UIXPTCZPFCVOQF-UHFFFAOYSA-N
form
powder
mp
58-60 °C (lit.)
storage temp.
2-8°C
Quality Level
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Application
2,3-Dimethoxy-5-methyl-p-benzoquinone has been used:
- as a tau protein fibrillization inducer to determine the regions of tau involved in the formation of paired helical filaments (PHFs)
- as a component in buffer B for cytochrome oxidation assay with subsaturating light
- in the RPMI-1640 medium for 2,3-bis-(2-methoxy-4-nitro-5-sulphenyl)-(2H)-tetrazolium-5-carboxanilide (XTT) assay to quantify antifungal activity
Coenzyme Q0 inhibits (via radical quenching) reactions of gamma-irradiation induced homolytic cleavage of O-glycoside bonds in polysaccharides. Coenzyme Q0 induces apoptosis and modulates the cell cycle in estrogen receptor negative breast cancer cells. It is toxic to other cells such as insulin producing cells.
Biochem/physiol Actions
2,3-Dimethoxy-5-methyl-p-benzoquinone (Coenzyme Q0) interacts with tau protein and aids in the formation of filamentous structure.
General description
2,3-Dimethoxy-5-methyl-p-benzoquinone (Coenzyme Q0 or DMM) is present in all the cells including neural cells.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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The Photosynthetic Bacterial Reaction Center: Structure and Dynamics, 114-114 (2013)
In vitro tau fibrillization: mapping protein regions
Santa-Maria I, et al.
Biochimica et Biophysica Acta (BBA)-Molecular Basis of Disease, 1762(7), 683-692 (2006)
XTT assay of antifungal activity
Loures FV and Levitz SM
PLoS Pathogens, 5(15), e1543-e1543 (2015)
Yung-Fu Wang et al.
Bioelectrochemistry (Amsterdam, Netherlands), 69(1), 74-81 (2006-01-25)
Bioelectrocatalytic oxidation of acetate was investigated under anaerobic conditions by using Escherichia coli K-12 (IFO 3301) cells cultured on aerobic media containing poly-peptone, glucose or acetate as the sole carbon source. It was found that all E. coli cells cultured
J J Poderoso et al.
Free radical biology & medicine, 26(7-8), 925-935 (1999-05-08)
The reaction of nitric oxide (*NO) with ubiquinol-0 and ubiquinol-2, short-chain analogs of coenzyme Q, was examined in anaerobic and aerobic conditions in terms of formation of intermediates and stable molecular products. The chemical reactivity of ubiquinol-0 and ubiquinol-2 towards
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