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2-hydroxypentanedioic acid

Product Name
2-hydroxypentanedioic acid
CAS No.
40951-21-1
Chemical Name
2-hydroxypentanedioic acid
Synonyms
2-HG (sodium salt);Disodium 2-hydroxyglutarate;Disodium 2-hydroxypentanedioate;α-Hydroxyglutaric acid (sodium);α-Hydroxyglutaric acid (disodium);2-Hydroxyglutaric Acid (sodium salt);DL-ALPHA-HYDROXYGLUTARIC ACID DISODI;α-Hydroxyglutaric Acid (sodium salt);2-Hydroxyglutaric Acid Disodium Salt;α-Hydroxyglutaric Acid (sodium salt)
CBNumber
CB71456168
Molecular Formula
C5H9NaO5
Formula Weight
172.11
MOL File
40951-21-1.mol
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2-hydroxypentanedioic acid Property

Melting point:
>290?C (dec.)
storage temp. 
2-8°C 2-8°C
solubility 
Methanol (Slightly), Water (Slightly)
form 
Solid
color 
White to Off-White
Water Solubility 
Soluble to 100 mM in water
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Safety

WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
94577
Product name
DL-α-Hydroxyglutaric acid disodium salt
Purity
≥95.0% (GC)
Packaging
100mg
Price
$177
Updated
2024/03/01
Sigma-Aldrich
Product number
94577
Product name
DL-α-Hydroxyglutaric acid disodium salt
Purity
≥95.0% (GC)
Packaging
500mg
Price
$687
Updated
2024/03/01
Cayman Chemical
Product number
16374
Product name
α-Hydroxyglutaric Acid (sodium salt)
Purity
≥95%
Packaging
10mg
Price
$49
Updated
2024/03/01
Cayman Chemical
Product number
16374
Product name
α-Hydroxyglutaric Acid (sodium salt)
Purity
≥95%
Packaging
25mg
Price
$109
Updated
2024/03/01
Cayman Chemical
Product number
16374
Product name
α-Hydroxyglutaric Acid (sodium salt)
Purity
≥95%
Packaging
100mg
Price
$403
Updated
2024/03/01
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2-hydroxypentanedioic acid Chemical Properties,Usage,Production

Description

α-Hydroxyglutaric acid (2-HG) is an α-hydroxy acid. It is metabolized to 2-oxoglutarate by D- and L-2-hydroxyglutarate dehydrogenases, and mutations in these enzymes lead to 2-hydroxyglutaric aciduria, a neurometabolic disorder characterized by increased levels of L-2-hydroxyglutaric acid . 2-HG can also be metabolized from isocitrate by mutated forms of isocitrate dehydrogenase 1 (IDH1) and IDH2. 2-HG is structurally similar to α-ketoglutarate, the product of wild-type isocitrate dehydrogenases, and competitively inhibits α-ketoglutarate-dependent dioxygenases, including histone lysine demethylases and DNA hydroxylases.

Chemical Properties

White to Off-White Solid

Uses

2-Hydroxyglutaric acid is a potential inhibitor of glutamate carboxypeptidase.

Biochem/physiol Actions

D-(or R-) enantiomer of α-hydroxyglutaric acid is a cancer related biomarker of diagnostic value, whereas the L-(or S-) enantiomer of α-hydroxyglutaric acid is a biomarker for certain neurometabolic, inherited disorder diseases. It has no known physiological function in eukaryotes. It is toxic to the brain and increases the susceptibility to develop brain tumors.

in vitro

in humans the enzyme hydroxyacid-oxoacid transhydrogenase catalyzed the formation of d-α-hydroxyglutaric acid, while d-α-hydroxyglutaric acid is catalyzed by 2-hydroxyglutarate synthase in bacteria. recent study discovered heterozygous somatic mutations in the genes encoding isocitrate dehydrogenase-1 and -2 (idh1 and idh2) and these mutations could disable the enzymes' ability to convert 2-ketoglutarate to d-α-hydroxyglutarate. the authors also found heterozygous germline mutations in idh2 that alter enzyme residue in patients with d-2-hydroxyglutaric aciduria, a neurometabolic disorder characterized by supraphysiological levels of d-α-hydroxyglutaric acid [1].

in vivo

previous animal study demonstrated that the overexpression of the isocitrate dehydrogenase-1 (idh1) mutation resulted in detectable levels of d-α-hydroxyglutaric acid in a mouse glioma model that could be measured in vivo and noninvasively by mrs. results showed that this mouse model system was of potential application in establishing the relationships among d-α-hydroxyglutaric acid levels and treatment effect, outcomes, as well as other related and necessary variables to validate d-α-hydroxyglutaric acid as a clinically important biomarker for glioma [2].

storage

Store at -20°C

References

[1] kranendijk m,struys ea,van schaftingen e,gibson km,kanhai wa,van der knaap ms,amiel j,buist nr,das am,de klerk jb,feigenbaum as,grange dk,hofstede fc,holme e,kirk ep,korman sh,morava e,morris a,smeitink j,sukhai rn,vallance h,jakobs c,salomons gs. idh2 mutations in patients with d-2-hydroxyglutaric aciduria. science.2010 oct 15;330(6002):336.
[2] lazovic j,soto h,piccioni d,lou jr,li s,mirsadraei l,yong w,prins r,liau lm,ellingson bm,cloughesy tf,lai a,pope wb. detection of 2-hydroxyglutaric acid in vivo by proton magnetic resonance spectroscopy in u87 glioma cells overexpressing isocitrate dehydrogenase-1 mutation. neuro oncol.2012 dec;14(12):1465-72.

2-hydroxypentanedioic acid Preparation Products And Raw materials

Raw materials

Preparation Products

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2-hydroxypentanedioic acid Suppliers

AdooQ BioScience, LLC
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+1 (866) 930-6790
Fax
+1 (866) 333-9607
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info@adooq.com
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United States
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2782
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TargetMol Chemicals Inc.
Tel
+1-781-999-5354 +1-00000000000
Email
marketing@targetmol.com
Country
United States
ProdList
32161
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58
United States Biological
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sales@advtechind.com
Country
United States
ProdList
6075
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58
ApexBio Technology
Tel
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Email
sales@apexbt.com
Country
United States
ProdList
6251
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58
Cayman Chemical Company
Tel
--
Fax
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Email
cayman@caymanchem.com
Country
United States
ProdList
6213
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Riedel-de Haen AG
Tel
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Fax
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Country
United States
ProdList
6773
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87

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