13095-47-1

Basic information

• Product Name: 2-hydroxypentanedioic acid
• Synonyms: 2-hydroxypentanedioic acid;D-2-Hydroxyglutaric acid;R-2-HYDROXYGLUTARATE;(R)-2-Hydroxyglutaric acid;(R)-alpha-Hydroxyglutaric acid;D-alpha-Hydroxyglutaric acid;Pentanedioic acid, 2-hydroxy-, (2R)-;D--Hydroxyglutaric Acid
• CAS NO: 13095-47-1
• Molecular Formula: C₅H₈O₅
• Molecular Weight: 146.10
• EINECS: 231-158-0
• Mol File: 13095-47-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 394.2 °C at 760 mmHg
• Flash Point: 206.4 °C
• Appearance: /
• Density: 1.508 g/cm³
• Vapor Pressure: 7.55E-08mmHg at 25°C
• Refractive Index: 1.519
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• PKA: 3.67±0.10(Predicted)
• CAS DataBase Reference: 2-hydroxypentanedioic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hydroxypentanedioic acid(13095-47-1)
• EPA Substance Registry System: 2-hydroxypentanedioic acid(13095-47-1)

Safety Data

• Hazardous Substances Data: 13095-47-1(Hazardous Substances Data)

Usage

Uses

2-Hydroxypentanedioic Acid is a mouse metabolite

InChI:InChI=1/C5H8O5/c6-3(5(9)10)1-2-4(7)8/h3,6H,1-2H2,(H,7,8)(H,9,10)/t3-/m1/s1

Synthetic route

D-Glutamic acid (6893-26-1) → (2R)-hydroxyglutaric acid (13095-47-1)

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;

(-)(S)-2-chloro-glutaric acid (4189-03-1, 149859-20-1) → (2R)-hydroxyglutaric acid (13095-47-1)

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

4-formyl-4-oxobutanoic acid (5976-90-9) → (2R)-hydroxyglutaric acid (13095-47-1)

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

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

D-Glucose (2280-44-6) → α-ketoglutaric acid (328-50-7) + (2R)-hydroxyglutaric acid (13095-47-1) + 2-oxo-propionic acid (127-17-3)

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;

pentadecane (629-62-9) → α-ketoglutaric acid (328-50-7) + (2R)-hydroxyglutaric acid (13095-47-1) + 2-oxo-propionic acid (127-17-3)

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;

Hexadecane (544-76-3) → α-ketoglutaric acid (328-50-7) + (2R)-hydroxyglutaric acid (13095-47-1) + 2-oxo-propionic acid (127-17-3)

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;

glycerol (56-81-5) → α-ketoglutaric acid (328-50-7) + (2R)-hydroxyglutaric acid (13095-47-1) + 2-oxo-propionic acid (127-17-3)

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;

4-formyl-4-oxobutanoic acid (5976-90-9) + enzyme-substance from peasseedlings → (2R)-hydroxyglutaric acid (13095-47-1)

4-formyl-4-oxobutanoic acid (5976-90-9) + escherichia coli → (2R)-hydroxyglutaric acid (13095-47-1)

4-formyl-4-oxobutanoic acid (5976-90-9) + liver-pulp → (2R)-hydroxyglutaric acid (13095-47-1)

4-formyl-4-oxobutanoic acid (5976-90-9) + living yeast → (2R)-hydroxyglutaric acid (13095-47-1)

4-formyl-4-oxobutanoic acid (5976-90-9) + muscle-pulp → (2R)-hydroxyglutaric acid (13095-47-1)

di-i-butyl 2-oxo-pentandioate (77630-52-5) → (2R)-hydroxyglutaric acid (13095-47-1) + L-hydroxyglutaric acid (13095-48-2)

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;

α-ketoglutaric acid (328-50-7) → (2R)-hydroxyglutaric acid (13095-47-1)

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;

isocitric acid (30810-51-6) → (2R)-hydroxyglutaric acid (13095-47-1)

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

methanol (67-56-1) + (2R)-hydroxyglutaric acid (13095-47-1) → D‐α‐hydroxyglutaric acid (55094-98-9)

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

(2R)-hydroxyglutaric acid (13095-47-1) + acetone (67-64-1) → 1,2-O-isopropylidene-D-malic acid

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

(2R)-hydroxyglutaric acid (13095-47-1) → D-(+)-2-hydroxyglutaric acid dihydrazide

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

(2R)-hydroxyglutaric acid (13095-47-1) → (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6)

Conditions	Yield
With dimethylsulfide borane complex In tetrahydrofuran

(2R)-hydroxyglutaric acid (13095-47-1) + water (7732-18-5) → d-butyrolactone-γ-carboxylic acid

Conditions	Yield
beim Verdampfen;

(2R)-hydroxyglutaric acid (13095-47-1) → (S)-5-tosyloxypentan-4-olide (58879-34-8)

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

(2R)-hydroxyglutaric acid (13095-47-1) → (R)-methyl-3-(oxiran-2-yl)propanoate (162600-37-5)

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

(2R)-hydroxyglutaric acid (13095-47-1) → C17H24NO9P

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

(2R)-hydroxyglutaric acid (13095-47-1) → C8H16NO7P (1356037-58-5)

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

(2R)-hydroxyglutaric acid (13095-47-1) → 2-{[(1-aminoethyl)(hydroxy)phosphoryl]oxy}-D-pentanedioic acid (1356037-43-8)

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

(2R)-hydroxyglutaric acid (13095-47-1) → C6H8O3 (81767-46-6)

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

(2R)-hydroxyglutaric acid (13095-47-1) → α-ketoglutaric acid (328-50-7)

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;

(2R)-hydroxyglutaric acid (13095-47-1) + (3R-trans)-dihydro-2,5-dioxofuran-3,4-diyl diacetate (6283-74-5) → C13H16O12

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

Upstream product

• 4189-03-1 (-)(S)-2-chloro-glutaric acid 
• 5976-90-9 4-formyl-4-oxobutanoic acid 
• 2280-44-6 D-Glucose 
• 544-76-3 Hexadecane 
• 30810-51-6 isocitric acid 
• 328-50-7 α-ketoglutaric acid 
• 77630-52-5 di-i-butyl 2-oxo-pentandioate 
• 56-81-5 glycerol 
• 629-62-9 pentadecane 
• 6893-26-1 D-Glutamic acid 

Downstream Products

• 328-50-7 α-ketoglutaric acid 
• 58879-34-8 (S)-5-tosyloxypentan-4-olide 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 

Relevant articles and documents

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(4R, 10S)-Methyl tri-isopropylsilyloxy-4-tert-butyldimethylsilyloxy-10-tert-amyloxy-11- undecanoate 1 has been synthesized from L-glutamic acid. This compound is a key intermediate in the total synthesis of annonacin, an acetogenin of Annonaceae.

Synthesis, characterization and activity of new phosphonate dipeptides as potential inhibitors of VanX

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Extracellular Production of D-(+)-2-Hydroxyglutaric Acid by Yarrowia lipilytica from Glucose under Aerobic, Thiamine-deficient Conditions

Under thiamine-deficient, aerobic culture conditions, Yarrowia lipolytica was found to produce D-(+)-2-hydroxyglutaric acid extracellularly in amounts of about 5 mg per ml of the culture filtrate, together with pyruvic and 2-ketoglutaric acids, from glucose or glycerol in a chemically defined medium.Under similar conditions, however, only a small amount of the hydroxy acid was produced from odd- or even-numbered n-alkanes.