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3-Deoxyglucosone

3-Deoxyglucosone structure

3-Deoxyglucosone 

structure
  • CAS No:

    4084-27-9

  • Formula:

    C6H10O5

  • Chemical Name:

    3-Deoxyglucosone

  • Synonyms:

    D-erythro-Hexos-2-ulose,3-deoxy-;D-erythro-Hexosulose,3-deoxy-;3-Deoxy-D-erythro-hexos-2-ulose;3-Deoxyglucosone;3-Deoxy-D-erythro-hexosulose;2-keto-3-Deoxyglucose;3-Deoxy-D-glucosone

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

3-Deoxyglucosone (3-Deoxy-D-glucosone) is a reactive intermediate of the Maillard reaction and the polyol pathway. 3-Deoxyglucosone rapidly reacts with protein amino groups to form advanced glycation end products (AGEs), such as imidazolone, it is the most specific AGE for 3-DG. 3-Deoxyglucosone synergizes with low glucose to potentiate GLP-1 secretion and is considered as a biomarker for diabetes[1][2][3].


3-deoxyglucosone is a deoxyketohexose comprising the open-chain form of D-glucose lacking the -OH group at the 3-position and having the keto group at the 2-position. It is a deoxyketohexose and a deoxyglucose.

3-Deoxyglucosone Basic Attributes

162.141

162.14

EXV5374VEY

DTXSID00193820

29329990

Characteristics

94.8

-2.38

1.4±0.1 g/cm3

73-75ºC

400.1±45.0 °C at 760 mmHg

209.9±25.2 °C

1.512

Soluble in water, methanol or hot ethanol.

Safety Information

NONH for all modes of transport

3

24/25

Xi

Hygroscopic

P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

H315

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Drug Information

2-keto-3-deoxyglucose

3-Deoxyglucosone Use and Manufacturing

An intermediate in the Maillard reaction of proteins with glucose, which is metabolised to 3-Deoxyfructose. An intermediate in the formation of pyrraline, which might contribute to a pathological effect, such as carcinogenesis

Computed Properties

Molecular Weight:162.14
XLogP3:-2.4
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:5
Exact Mass:162.05282342
Monoisotopic Mass:162.05282342
Topological Polar Surface Area:94.8
Heavy Atom Count:11
Complexity:144
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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