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D9150

Sigma-Aldrich

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:
605-94-7
Molecular Weight:
182.17
Beilstein/REAXYS Number:
1640422
EC Number:
210-100-8
MDL number:
MFCD00001595
UNSPSC Code:
12352204
PubChem Substance ID:
24894261
NACRES:
NA.51

form

powder

mp

58-60 °C (lit.)

storage temp.

2-8°C

SMILES string

COC1=C(OC)C(=O)C(C)=CC1=O

InChI

1S/C9H10O4/c1-5-4-6(10)8(12-2)9(13-3)7(5)11/h4H,1-3H3

InChI key

UIXPTCZPFCVOQF-UHFFFAOYSA-N

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General description

2,3-Dimethoxy-5-methyl-p-benzoquinone (Coenzyme Q0 or DMM) is present in all the cells including neural cells.

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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)
The Photosynthetic Bacterial Reaction Center: Structure and Dynamics, 114-114 (2013)
XTT assay of antifungal activity
Loures FV and Levitz SM
PLoS Pathogens, 5(15), e1543-e1543 (2015)
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
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
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