D-2-Hydroxyglutaric acid supplier

Name
2-hydroxypentanedioic acid
EINECS 231-158-0
CAS No. 13095-47-1
Article Data15
CAS DataBase
Density 1.508 g/cm³
Solubility
Melting Point
Formula C₅H₈O₅
Boiling Point 394.2 °C at 760 mmHg
Molecular Weight 148.116
Flash Point 206.4 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Glutaricacid, 2-hydroxy-, D- (8CI);Pentanedioic acid, 2-hydroxy-, (R)-;(R)-2-Hydroxyglutaric acid;(R)-a-Hydroxyglutaric acid;D-a-Hydroxyglutaric acid;
PSA 94.83000
LogP -0.70330

Synthetic route

: 6893-26-1
D-Glutamic acid

: 13095-47-1
(2R)-hydroxyglutaric acid

Conditions

Conditions	Yield
With hydrogenchloride; acetic acid; sodium nitrite
With oxonium; sodium nitrite In water
Multi-step reaction with 2 steps 1: concentrated hydrochloric acid; nitrosyl chloride 2: water View Scheme
With sulfuric acid; sodium nitrite In water at 20℃; for 27h; Cooling with ice;

: 4189-03-1, 149859-20-1
(-)(S)-2-chloro-glutaric acid

: 13095-47-1
(2R)-hydroxyglutaric acid

Conditions

Conditions	Yield
With sodium hydroxide
With water; silver(l) oxide
With water

: 5976-90-9
4-formyl-4-oxobutanoic acid

: 13095-47-1
(2R)-hydroxyglutaric acid

Conditions

Conditions	Yield
durch Einw. von Escherichia coli;
durch Einw. von lebender Hefe;
dursch Einw. von Leber- oder Muskelbrei sowie Muskelextrakt;
weniger einheitliche Praeparate bilden sich bei der Einw. eines aus Erbsenkeimlingen hergestellten Fermentpraeparates;

: (R)-2-((R)-2-Benzyloxycarbonylamino-3-phenyl-propionyloxy)-pentanedioic acid 1-tert-butyl ester 5-(4-nitro-benzyl) ester

: 13095-47-1
(2R)-hydroxyglutaric acid

Conditions

Conditions	Yield
(i) HBr, AcOH, (ii) H2, Pd, MeOH, (iii) aq. HCl; Multistep reaction;

: 2280-44-6
D-Glucose

A: 328-50-7
α-ketoglutaric acid

B: 13095-47-1
(2R)-hydroxyglutaric acid

C: 127-17-3
2-oxo-propionic acid

Conditions

Conditions	Yield
With ammonium iron (II) sulfate; potassium dihydrogenphosphate; ammonium succinate; D-glucose; Thiamine hydrochloride; magnesium sulfate In water at 26℃; for 144h; Yarrowia lipolytica R-2; Yield given. Yields of byproduct given;
With ammonium iron (II) sulfate; potassium dihydrogenphosphate; ammonium succinate; D-glucose; Thiamine hydrochloride; magnesium sulfate In water at 26℃; for 144h; Yarrowia lipolytica IFO 1659; Yield given. Yields of byproduct given;

...Expand

: 629-62-9
pentadecane

A: 328-50-7
α-ketoglutaric acid

B: 13095-47-1
(2R)-hydroxyglutaric acid

C: 127-17-3
2-oxo-propionic acid

Conditions

Conditions	Yield
With ammonium iron (II) sulfate; potassium dihydrogenphosphate; ammonium succinate; D-glucose; Thiamine hydrochloride; magnesium sulfate In water at 26℃; for 144h; Yarrowia lipolytica IFO 1659; Yield given. Yields of byproduct given;
With ammonium iron (II) sulfate; potassium dihydrogenphosphate; ammonium succinate; D-glucose; Thiamine hydrochloride; magnesium sulfate In water at 26℃; for 144h; Yarrowia lipolytica R-2; Yield given. Yields of byproduct given;

...Expand

: 544-76-3
Hexadecane

A: 328-50-7
α-ketoglutaric acid

B: 13095-47-1
(2R)-hydroxyglutaric acid

C: 127-17-3
2-oxo-propionic acid

Conditions

Conditions	Yield
With ammonium iron (II) sulfate; potassium dihydrogenphosphate; ammonium succinate; D-glucose; Thiamine hydrochloride; magnesium sulfate In water at 26℃; for 144h; Yarrowia lipolytica IFO 1659; Yield given. Yields of byproduct given;
With ammonium iron (II) sulfate; potassium dihydrogenphosphate; ammonium succinate; D-glucose; Thiamine hydrochloride; magnesium sulfate In water at 26℃; for 144h; Yarrowia lipolytica R-2; Yield given. Yields of byproduct given;

...Expand

: 56-81-5
glycerol

A: 328-50-7
α-ketoglutaric acid

B: 13095-47-1
(2R)-hydroxyglutaric acid

C: 127-17-3
2-oxo-propionic acid

Conditions

Conditions	Yield
With ammonium iron (II) sulfate; potassium dihydrogenphosphate; ammonium succinate; D-glucose; Thiamine hydrochloride; magnesium sulfate In water at 26℃; for 144h; Yarrowia lipolytica IFO 1659; Yield given. Yields of byproduct given;

...Expand

: 5976-90-9
4-formyl-4-oxobutanoic acid

enzyme-substance from peasseedlings: enzyme-substance from peasseedlings

: 13095-47-1
(2R)-hydroxyglutaric acid

: 5976-90-9
4-formyl-4-oxobutanoic acid

escherichia coli: escherichia coli

: 13095-47-1
(2R)-hydroxyglutaric acid

: 5976-90-9
4-formyl-4-oxobutanoic acid

liver-pulp: liver-pulp

: 13095-47-1
(2R)-hydroxyglutaric acid

: 5976-90-9
4-formyl-4-oxobutanoic acid

living yeast: living yeast

: 13095-47-1
(2R)-hydroxyglutaric acid

: 5976-90-9
4-formyl-4-oxobutanoic acid

muscle-pulp: muscle-pulp

: 13095-47-1
(2R)-hydroxyglutaric acid

: 77630-52-5
di-i-butyl 2-oxo-pentandioate

A: 13095-47-1
(2R)-hydroxyglutaric acid

B: 13095-48-2
L-hydroxyglutaric acid

Conditions

Conditions	Yield
Stage #1: di-i-butyl 2-oxo-pentandioate With Mucor rouxii yeast-like cells In hexane; water at 28℃; for 40h; Stage #2: With Candida antarctica lipase B; phosphate buffer at 30℃; pH=7; Title compound not separated from byproducts;

: 328-50-7
α-ketoglutaric acid

: 13095-47-1
(2R)-hydroxyglutaric acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: Novozym 435 lipase B from Candida antarctica / 30 °C 2.1: Mucor rouxii yeast-like cells / hexane; H2O / 40 h / 28 °C 2.2: Candida antarctica lipase B; phosphate buffer / 30 °C / pH 7 View Scheme
With mutant isocitrate hydrogenase; NADPH; magnesium chloride In aq. phosphate buffer pH=7.5; Enzymatic reaction;

: 30810-51-6
isocitric acid

: 13095-47-1
(2R)-hydroxyglutaric acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: magnesium chloride; NADP; wild type isocitrate hydrogenase / aq. phosphate buffer / pH 7.5 / Enzymatic reaction 2: magnesium chloride; NADPH; mutant isocitrate hydrogenase / aq. phosphate buffer / pH 7.5 / Enzymatic reaction View Scheme

: 67-56-1
methanol

: 13095-47-1
(2R)-hydroxyglutaric acid

: 55094-98-9
D‐α‐hydroxyglutaric acid

Conditions

Conditions	Yield
Stage #1: methanol With thionyl chloride at 0℃; for 1h; Stage #2: (2R)-hydroxyglutaric acid at 20 - 65℃; for 7h;	58%

: 13095-47-1
(2R)-hydroxyglutaric acid

: 67-64-1
acetone

: 1,2-O-isopropylidene-D-malic acid

Conditions

Conditions	Yield
With toluene-4-sulfonic acid at 20℃; for 24h;	50%

: 13095-47-1
(2R)-hydroxyglutaric acid

: D-(+)-2-hydroxyglutaric acid dihydrazide

Conditions

Conditions	Yield
With diazomethane; hydrazine hydrate 1.) ether, 2.) ether, reflux, 5 h; Multistep reaction;

: 13095-47-1
(2R)-hydroxyglutaric acid

: 32780-06-6
(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

Conditions

Conditions	Yield
With dimethylsulfide borane complex In tetrahydrofuran

: 13095-47-1
(2R)-hydroxyglutaric acid

: 7732-18-5
water

d-butyrolactone-γ-carboxylic acid: d-butyrolactone-γ-carboxylic acid

Conditions

Conditions	Yield
beim Verdampfen;

: 13095-47-1
(2R)-hydroxyglutaric acid

: 58879-34-8
(S)-5-tosyloxypentan-4-olide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: BH3*Me2S / tetrahydrofuran 2: pyridine View Scheme

: 13095-47-1
(2R)-hydroxyglutaric acid

: 162600-37-5
(R)-methyl-3-(oxiran-2-yl)propanoate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: BH3*Me2S / tetrahydrofuran 2: pyridine 3: methanol View Scheme

: 13095-47-1
(2R)-hydroxyglutaric acid

: C17H24NO9P

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: thionyl chloride / 1 h / 0 °C 1.2: 7 h / 20 - 65 °C 2.1: triethylamine / chloroform / 72 h / 20 °C View Scheme

: 13095-47-1
(2R)-hydroxyglutaric acid

: 1356037-58-5
C8H16NO7P

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: thionyl chloride / 1 h / 0 °C 1.2: 7 h / 20 - 65 °C 2.1: triethylamine / chloroform / 72 h / 20 °C 3.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 20 °C View Scheme

: 13095-47-1
(2R)-hydroxyglutaric acid

: 1356037-43-8
2-{[(1-aminoethyl)(hydroxy)phosphoryl]oxy}-D-pentanedioic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: thionyl chloride / 1 h / 0 °C 1.2: 7 h / 20 - 65 °C 2.1: triethylamine / chloroform / 72 h / 20 °C 3.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 20 °C 4.1: methanol; lithium hydroxide / 48 h / 20 °C 4.2: cation exchange resin View Scheme

: 13095-47-1
(2R)-hydroxyglutaric acid

: 81767-46-6
C6H8O3

Conditions

Conditions	Yield
With boron trifluoride In methanol at 105℃; for 0.75h;

: 13095-47-1
(2R)-hydroxyglutaric acid

: 328-50-7
α-ketoglutaric acid

Conditions

Conditions	Yield
With [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide]; D-2-HG dehydrogenase; phenazine methosulfate at 37℃; for 0.666667h; Enzymatic reaction;

: 13095-47-1
(2R)-hydroxyglutaric acid

: 6283-74-5
(3R-trans)-dihydro-2,5-dioxofuran-3,4-diyl diacetate

: C13H16O12

Conditions

Conditions	Yield
With acetic acid In dichloromethane at 75℃; for 0.5h; Reagent/catalyst;

D-2-Hydroxyglutaric acid Specification

The Pentanedioic acid,2-hydroxy-, (2R)- with CAS registry number of 13095-47-1 is also known as D-2-Hydroxyglutaric acid. The IUPAC name is (2R)-2-Hydroxypentanedioate. In addition, the formula is C₅H₈O₅ and the molecular weight is 146.10.

Physical properties about Pentanedioic acid,2-hydroxy-, (2R)- are: (1)ACD/LogP: -1.45; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 1; (5)ACD/KOC (pH 7.4): 1; (6)#H bond acceptors: 5; (7)#H bond donors: 3; (8)#Freely Rotating Bonds: 5; (9)Index of Refraction: 1.519; (10)Molar Refractivity: 29.83 cm³; (11)Molar Volume: 98.2 cm³; (12)Surface Tension: 74.7 dyne/cm; (13)Density: 1.508 g/cm³; (14)Flash Point: 206.4 °C; (15)Enthalpy of Vaporization: 74.48 kJ/mol; (16)Boiling Point: 394.2 °C at 760 mmHg; (17)Vapour Pressure: 7.55E-08 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C(CC(=O)[O-])C(C(=O)[O-])O
2. Isomeric SMILES: C(CC(=O)[O-])[C@H](C(=O)[O-])O
3. InChI: InChI=1S/C5H8O5/c6-3(5(9)10)1-2-4(7)8/h3,6H,1-2H2,(H,7,8)(H,9,10)/p-2/t3-/m1/s1
4. InChIKey: HWXBTNAVRSUOJR-GSVOUGTGSA-L

Product Name

2-hydroxypentanedioic acid

Synthetic route

D-2-Hydroxyglutaric acid Specification

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