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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:
1640422
EC Number:
210-100-8
MDL number:
MFCD00001595
UNSPSC Code:
12352204
PubChem Substance ID:
24894261
NACRES:
NA.51

Quality Level

200

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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Stanislaw Schmidt et al.
Pathogens (Basel, Switzerland), 8(4) (2019-12-05)
Immunosuppressive drugs are administered to a number of patients; e.g., to allogeneic hematopoietic stem cell transplant recipients. Immunosuppressive drugs impair the immune system and thus increase the risk of invasive fungal disease, but may exhibit antifungal activity at the same
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
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)
Stefania Fiorcari et al.
Frontiers in immunology, 11, 2158-2158 (2020-09-29)
Infections represent a cause of morbidity and mortality in patients affected by chronic lymphocytic leukemia (CLL). Introduction of new drugs in CLL clinical practice has showed impressive efficacy, in particular those targeting BTK. Among the consistent clinical data, an increasing
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