Product Name

  • Name

    Diethyl 3-hydroxyglutarate

  • EINECS 250-992-6
  • CAS No. 32328-03-3
  • Article Data16
  • CAS DataBase
  • Density 1.122 g/cm3
  • Solubility
  • Melting Point 48oC
  • Formula C9H16O5
  • Boiling Point 256.5 °C at 760 mmHg
  • Molecular Weight 204.223
  • Flash Point 110.7 °C
  • Transport Information
  • Appearance Light yellow to colorless liquid
  • Safety 23-24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 32328-03-3 (Diethyl 3-hydroxyglutarate)
  • Hazard Symbols
  • Synonyms Glutaricacid, 3-hydroxy-, diethyl ester (6CI,7CI);Pentanedioic acid, 3-hydroxy-,diethyl ester (9CI);3-Hydroxyglutaric acid diethyl ester;Diethyl 3-hydroxypentanedioate;NSC 62681;
  • PSA 72.83000
  • LogP 0.25370

Synthetic route

diethyl 1,3-acetonedicarboxylate
105-50-0

diethyl 1,3-acetonedicarboxylate

diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

Conditions
ConditionsYield
With sodium tetrahydroborate; ethanol at 0℃; for 0.05h;95%
With sodium amalgam
With 1,4-dioxane; nickel Hydrogenation;
diethyl 3-hydroxypentanedioate
638-18-6

diethyl 3-hydroxypentanedioate

ethanol
64-17-5

ethanol

diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

Conditions
ConditionsYield
With sulfuric acid
With sulfuric acid
ethanol
64-17-5

ethanol

3-hydroxyglutaronitrile
13880-89-2

3-hydroxyglutaronitrile

diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

Conditions
ConditionsYield
With sulfuric acid at 90 - 100℃;
With hydrogenchloride In diethyl ether
3-hydroxyglutaronitrile
13880-89-2

3-hydroxyglutaronitrile

diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

allyl bromide
106-95-6

allyl bromide

diethyl 1,3-acetonedicarboxylate
105-50-0

diethyl 1,3-acetonedicarboxylate

diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

Conditions
ConditionsYield
With sodium ethanolate 1.) EtOH, r.t., overnight, 2.) baker's yeast, H2O, 30 deg C, 72 h; Yield given. Multistep reaction;
diethyl 1,3-acetonedicarboxylate
105-50-0

diethyl 1,3-acetonedicarboxylate

Raney nickel

Raney nickel

diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

Conditions
ConditionsYield
Hydrogenation;
ethanol
64-17-5

ethanol

triethylamine
121-44-8

triethylamine

diethyl 1,3-acetonedicarboxylate
105-50-0

diethyl 1,3-acetonedicarboxylate

Raney nickel

Raney nickel

A

diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

B

pentane-1,3,5-triol
4328-94-3

pentane-1,3,5-triol

Conditions
ConditionsYield
at 125℃; under 250073 Torr; Hydrogenation;
...Expand
acetonedicarboxylic acid
542-05-2

acetonedicarboxylic acid

diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: sodium amalgam
View Scheme
3-oxopentanedioic acid dimethyl ester
1830-54-2

3-oxopentanedioic acid dimethyl ester

diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: NaBH4 / methanol
2: KOH / methanol
3: H2SO4
View Scheme
dimethyl 3-hydroxypentanedioate
7250-55-7

dimethyl 3-hydroxypentanedioate

diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: KOH / methanol
2: H2SO4
View Scheme
diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

1-(Trimethylsilyl)imidazole
18156-74-6

1-(Trimethylsilyl)imidazole

diethyl 3-<(trimethylsilyl)oxy>pentanedioate
91424-41-8

diethyl 3-<(trimethylsilyl)oxy>pentanedioate

Conditions
ConditionsYield
In dichloromethane for 26.5h; Ambient temperature;100%
for 12.5h; Ambient temperature;
diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

3-[[(1,1-Dimethylethyl)dimethylsilyl]-oxy]pentanedioic acid,diethyl ester
91424-39-4

3-[[(1,1-Dimethylethyl)dimethylsilyl]-oxy]pentanedioic acid,diethyl ester

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane Inert atmosphere;99%
With 1H-imidazole In dichloromethane99%
With 1H-imidazole In dichloromethane for 18h; Ambient temperature;95%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

diethyl 3-<(trimethylsilyl)oxy>pentanedioate
91424-41-8

diethyl 3-<(trimethylsilyl)oxy>pentanedioate

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane at 20℃; Inert atmosphere;99%
With 1H-imidazole In dichloromethane at 20℃;99%
With 1H-imidazole In dichloromethane at 20 - 25℃; for 16h; Inert atmosphere;
diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

(3S)-5-ethoxy-3-hydroxy-5-oxopentanoic acid
95310-87-5

(3S)-5-ethoxy-3-hydroxy-5-oxopentanoic acid

Conditions
ConditionsYield
With Candida antarctica lipase B; water; sodium hydroxide at 40℃; for 0.5h; pH=7; Kinetics; pH-value; Temperature; Concentration; aq. phosphate buffer; optical yield given as %ee; enantioselective reaction;98.5%
With Esterase 30 000 In cyclohexane; water at 25℃; for 3h; pH 7.5 (0.1 M phosphat buffer);94%
With Arthrobacter sp (ATCC 19140) In various solvent(s) for 48h; Product distribution; Microorganism: Corynebacterium equi. Object: enantioselective hydrolysis;38%
In various solvent(s) for 48h; Corynebacterium equi (IFO-3730) or Arthrobacter sp (ATCC 19140); Yield given;
With lipase B from Candida antarctica at 20℃; for 1h; pH=7; aq. phosphate buffer; Inert atmosphere; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;
diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

pentane-1,3,5-triol
4328-94-3

pentane-1,3,5-triol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 66℃; for 72h; Inert atmosphere;97%
Stage #1: diethyl 3-hydroxyglutarate With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃;
Stage #2: With ammonium chloride In tetrahydrofuran at -78℃; Cooling with acetone-dry ice;		78%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 3h;65%
diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

Methoxyacetyl chloride
38870-89-2

Methoxyacetyl chloride

3-(2-Methoxy-acetoxy)-pentanedioic acid diethyl ester
483299-14-5

3-(2-Methoxy-acetoxy)-pentanedioic acid diethyl ester

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃;97%
diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

3-(tert-butyldiphenylsilanyloxy)pentanedioic acid diethyl ester
923027-81-0

3-(tert-butyldiphenylsilanyloxy)pentanedioic acid diethyl ester

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane at 20℃; for 16h;96%
diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

(S)-3-hydroxyglutaric acid monoamidemonoethyl ester

(S)-3-hydroxyglutaric acid monoamidemonoethyl ester

Conditions
ConditionsYield
Novozym 43595%
diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

allyl ethyl carbonate
1469-70-1

allyl ethyl carbonate

diethyl 3-(allyloxy)glutarate

diethyl 3-(allyloxy)glutarate

Conditions
ConditionsYield
With bis(η3-allyl-μ-chloropalladium(II)); 1,4-di(diphenylphosphino)-butane In toluene at 110℃; for 16h; Inert atmosphere;95%
diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

benzaldehyde
100-52-7

benzaldehyde

diethyl 3-(benzyloxy)pentanedioate
838906-52-8

diethyl 3-(benzyloxy)pentanedioate

Conditions
ConditionsYield
Stage #1: diethyl 3-hydroxyglutarate; benzaldehyde With Hexamethyldisiloxane; trimethylsilyl trifluoromethanesulfonate In tetrahydrofuran at -30℃; for 2h; Inert atmosphere;
Stage #2: With triethylsilane In tetrahydrofuran at -30℃; for 16h; Inert atmosphere;
Stage #3: With sodium tetrahydroborate In methanol at 0℃; for 1h; Inert atmosphere;		93%
Stage #1: diethyl 3-hydroxyglutarate; benzaldehyde With trimethylsilyl trifluoromethanesulfonate; C6H18OSSi In tetrahydrofuran for 2h; Cooling;
Stage #2: With triethylsilane In tetrahydrofuran for 16h; Cooling;
Stage #3: With methanol; sodium tetrahydroborate at 0℃; for 1h;		93%
diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

3-hydroxyglutaramide
16072-48-3

3-hydroxyglutaramide

Conditions
ConditionsYield
With ammonia In methanol at 20℃; for 144h;90%
With ammonia
methanol
67-56-1

methanol

diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

dimethyl 3-hydroxypentanedioate
7250-55-7

dimethyl 3-hydroxypentanedioate

Conditions
ConditionsYield
scandium tris(trifluoromethanesulfonate) at 64℃; for 24h;89%
diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

acetic anhydride
108-24-7

acetic anhydride

ethyl 3-acetoxypentanedioate
91967-12-3

ethyl 3-acetoxypentanedioate

Conditions
ConditionsYield
With pyridine Ambient temperature;88%
Benzyloxymethyl chloride
3587-60-8

Benzyloxymethyl chloride

diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

diethyl 3-(benzyloxymethyloxy)glutarate
1607830-30-7

diethyl 3-(benzyloxymethyloxy)glutarate

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Inert atmosphere;85%
With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;85%
With tetrabutyl-ammonium chloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h;60%
diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

diethyl 3-hydroxypentanedioate
638-18-6

diethyl 3-hydroxypentanedioate

Conditions
ConditionsYield
With sodium hydroxide In methanol; water for 60h; Ambient temperature;84%
With potassium hydroxide In ethanol
diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

β-naphthaldehyde
66-99-9

β-naphthaldehyde

diethyl 3-(naphth-2-yl-methoxy)glutarate

diethyl 3-(naphth-2-yl-methoxy)glutarate

Conditions
ConditionsYield
Stage #1: diethyl 3-hydroxyglutarate; β-naphthaldehyde With Hexamethyldisiloxane; trimethylsilyl trifluoromethanesulfonate In tetrahydrofuran at -30℃; for 2h; Inert atmosphere;
Stage #2: With triethylsilane In tetrahydrofuran at -30℃; for 16h; Inert atmosphere;
Stage #3: With sodium tetrahydroborate In methanol at 0℃; for 1h; Inert atmosphere;		82%
Stage #1: diethyl 3-hydroxyglutarate; β-naphthaldehyde With trimethylsilyl trifluoromethanesulfonate; C6H18OSSi In tetrahydrofuran for 2h; Cooling;
Stage #2: With triethylsilane for 16h; Cooling;
Stage #3: With methanol; sodium tetrahydroborate at 0℃; for 1h;		82%
diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

methyl iodide
74-88-4

methyl iodide

diethyl 3-methoxypentanedioate

diethyl 3-methoxypentanedioate

Conditions
ConditionsYield
With silver(l) oxide In N,N-dimethyl-formamide at 20℃; for 72h;82%
diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

O-benzyl 2,2,2-trichloroacetimidate
81927-55-1

O-benzyl 2,2,2-trichloroacetimidate

diethyl 3-(benzyloxy)pentanedioate
838906-52-8

diethyl 3-(benzyloxy)pentanedioate

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In dichloromethane; cyclohexane at 0℃; for 24h;79%
With trifluorormethanesulfonic acid In dichloromethane; cyclohexane at 20℃; for 20h; Inert atmosphere;78%
diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

(4-chlorophenyl)(pyridin-2-yl)methyl 2,2,2-trichloroacetimidate

(4-chlorophenyl)(pyridin-2-yl)methyl 2,2,2-trichloroacetimidate

diethyl 3-[(4-chlorophenyl)(pyridin-2-yl)methoxy]pentanedioate

diethyl 3-[(4-chlorophenyl)(pyridin-2-yl)methoxy]pentanedioate

Conditions
ConditionsYield
With copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 20℃; for 24h; Molecular sieve; Inert atmosphere; Cooling with ice;73%
diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

3-(tert-Butyl-dimethyl-silanyloxy)-pentanedioic acid
113794-48-2

3-(tert-Butyl-dimethyl-silanyloxy)-pentanedioic acid

Conditions
ConditionsYield
Stage #1: tert-butyldimethylsilyl chloride With 1H-imidazole In dichloromethane at 20 - 30℃; for 1 - 2h;
Stage #2: diethyl 3-hydroxyglutarate In dichloromethane at 20 - 30℃; for 4 - 6h;
Stage #3: With hydrogenchloride; sodium hydroxide; water more than 3 stages;		71%
diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

(3R)-5-ethoxy-3-hydroxy-5-oxopentanoic acid
95310-88-6

(3R)-5-ethoxy-3-hydroxy-5-oxopentanoic acid

Conditions
ConditionsYield
With Acinetobacter lowfii In various solvent(s) for 48h; Product distribution; Microrganism: Soil isolate S-29. Object: enantioselective hydrolysis.;70%
With disodium hydrogenphosphate; α-chymotrypsin
In various solvent(s) for 48h; Acinetobacter lowfii, or Soil isolate S-29; Yield given;
Multi-step reaction with 3 steps
1: zinc perchlorate / 2 h / 20 °C
2: α-chymotrypsin / aq. buffer / 27 h / 20 °C / pH 8 / Enzymatic reaction
3: immobilized Cephalosporin C acetyl esterase / aq. buffer / 20 °C / pH 8 / Enzymatic reaction
View Scheme
diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

S-ethyl 3-phenylpropionic acid thioester
30911-16-1

S-ethyl 3-phenylpropionic acid thioester

3-(3-Phenyl-propionyloxy)-pentanedioic acid diethyl ester
130260-30-9

3-(3-Phenyl-propionyloxy)-pentanedioic acid diethyl ester

Conditions
ConditionsYield
With lithium tetrafluoroborate In acetonitrile Ambient temperature; Pt-electrodes, 50 mA;64%
diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

diethyl 3-(methoxymethoxy)glutarate

diethyl 3-(methoxymethoxy)glutarate

Conditions
ConditionsYield
With tetrabutyl-ammonium chloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h;64%
diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

but-2-ynyl 2,2,2-trichloroacetimidate
59402-95-8

but-2-ynyl 2,2,2-trichloroacetimidate

diethyl 3-(but-2-yn-1yloxy)glutarate

diethyl 3-(but-2-yn-1yloxy)glutarate

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 1h;60%
diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

methyl 1,8-dihydroxy-3-(methoxycarbonylmethyl)naphthalene-2-carboxylate
107182-04-7

methyl 1,8-dihydroxy-3-(methoxycarbonylmethyl)naphthalene-2-carboxylate

Conditions
ConditionsYield
Stage #1: diethyl 3-hydroxyglutarate; acetoacetic acid methyl ester With lithium diisopropyl amide In tetrahydrofuran at -78℃; Claisen condensation;
Stage #2: With calcium acetate In tetrahydrofuran; methanol		57%
With n-butyllithium; calcium acetate; sodium hydride 1.) THF, hexane, 1 h, room temperature, 2.) MeOH, 2 h, reflux; Yield given. Multistep reaction;
diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

1-(1-imino-2,2,2-trichloroethoxy)-3-methyl-2-butene
104808-44-8

1-(1-imino-2,2,2-trichloroethoxy)-3-methyl-2-butene

A

diethyl 3-(3,3-dimethylallyloxy)glutarate

diethyl 3-(3,3-dimethylallyloxy)glutarate

B

diethyl 3-(1,1-dimethylallyloxy)glutarate

diethyl 3-(1,1-dimethylallyloxy)glutarate

Conditions
ConditionsYield
With scandium tris(trifluoromethanesulfonate) In dichloromethane at 20℃; for 0.5h;A 42%
B 24%
...Expand
diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

3-Phenylpropenol
104-54-1

3-Phenylpropenol

C18H24O5

C18H24O5

Conditions
ConditionsYield
Stage #1: diethyl 3-hydroxyglutarate With 1H-imidazole; chloro-trimethyl-silane Inert atmosphere;
Stage #2: 3-Phenylpropenol With triethylsilane; iron(III) chloride Reagent/catalyst; Inert atmosphere;		41%
benzyltrichloroacetimidate

benzyltrichloroacetimidate

diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

diethyl 3-(benzyloxy)pentanedioate
838906-52-8

diethyl 3-(benzyloxy)pentanedioate

Conditions
ConditionsYield
With trifluorormethanesulfonic acid35%
diethyl 3-hydroxyglutarate
32328-03-3

diethyl 3-hydroxyglutarate

benzyl bromide
100-39-0

benzyl bromide

diethyl 3-(benzyloxy)pentanedioate
838906-52-8

diethyl 3-(benzyloxy)pentanedioate

Conditions
ConditionsYield
With silver(l) oxide30%
With silver(l) oxide In acetonitrile for 14h; Heating;24%

Diethyl 3-hydroxyglutarate Specification

The Pentanedioic acid,3-hydroxy-, 1,5-diethyl ester, with CAS registry number 32328-03-3, belongs to the following product categories: (1)C8 to C9; (2)Carbonyl Compounds; (3)Esters. It has the systematic name of diethyl 3-hydroxypentanedioate. What's more, its EINECS is 250-992-6.

Physical properties of Pentanedioic acid,3-hydroxy-, 1,5-diethyl ester: (1)ACD/LogP: 0.29; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.29; (4)ACD/LogD (pH 7.4): 0.29; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 34.33; (8)ACD/KOC (pH 7.4): 34.33; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 9; (12)Polar Surface Area: 61.83 Å2; (13)Index of Refraction: 1.448; (14)Molar Refractivity: 48.78 cm3; (15)Molar Volume: 181.9 cm3; (16)Polarizability: 19.34×10-24cm3; (17)Surface Tension: 38.6 dyne/cm; (18)Enthalpy of Vaporization: 57.39 kJ/mol; (19)Vapour Pressure: 0.00229 mmHg at 25°C.

Uses of Pentanedioic acid,3-hydroxy-, 1,5-diethyl ester: it can be used to produce (R)-ethyl hydrogen-3-hydroxyglutarate. This reaction will need reagents a-chymotrypsin, aq. Na2HPO4.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OCC)CC(O)CC(=O)OCC
(2)InChI: InChI=1/C9H16O5/c1-3-13-8(11)5-7(10)6-9(12)14-4-2/h7,10H,3-6H2,1-2H3
(3)InChIKey: OLLQYIBTJXUEEX-UHFFFAOYAA
(4)Std. InChI: InChI=1S/C9H16O5/c1-3-13-8(11)5-7(10)6-9(12)14-4-2/h7,10H,3-6H2,1-2H3
(5)Std. InChIKey: OLLQYIBTJXUEEX-UHFFFAOYSA-N

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