6168-83-8

Basic information

• Product Name: (S)-3-HYDROXYBUTYRIC ACID
• Synonyms: (S)-(+)-3-HYDROXYBUTYRIC ACID;(S)-3-HYDROXYBUTYRIC ACID;(S)-3-Hydroxybutyrate;(3S)-3-hydroxybutanoic acid;(S)-3-Hydroxybutanoic acid;[S,(+)]-3-Hydroxybutanoic acid;L-3-Hydroxybutyric acid;(3S)-3-hydroxybutyric acid
• CAS NO: 6168-83-8
• Molecular Formula: C₄H₈O₃
• Molecular Weight: 104.1
• EINECS: 228-209-4
• Product Categories: Carboxylic Acids;Chiral Building Blocks;Organic Building Blocks
• Mol File: 6168-83-8.mol
• Article Data: 36

Chemical Properties

• Melting Point: 45-48 °C
• Boiling Point: 269.2 °C at 760 mmHg
• Flash Point: 121 °C
• Appearance: /
• Density: 1.195 g/cm³
• Vapor Pressure: 0.000979mmHg at 25°C
• Refractive Index: 1.455
• Storage Temp.: 2-8°C
• PKA: 4.36±0.10(Predicted)
• BRN: 1720567
• CAS DataBase Reference: (S)-3-HYDROXYBUTYRIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-HYDROXYBUTYRIC ACID(6168-83-8)
• EPA Substance Registry System: (S)-3-HYDROXYBUTYRIC ACID(6168-83-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 6168-83-8(Hazardous Substances Data)

Usage

Definition

ChEBI: The S-enantiomer of 3-hydroxybutyric acid; a normal human metabolite, that has been found elevated in geriatric patients remitting from depression.

InChI:InChI=1/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m0/s1

Synthetic route

(S)-(-)-β-methyl-β-propiolactone (65058-82-4) → (S)-3-Hydroxybutanoic Acid (6168-83-8)

Conditions	Yield
With sodium hydroxide In water at 0℃; for 0.333333h;	71%
With hydrogenchloride In diethyl ether; water for 18h; pH=2;	63%

(S)-3-hydroxybutyric acid methyl ester (53562-86-0) → (S)-3-Hydroxybutanoic Acid (6168-83-8)

Conditions	Yield
With sodium hydroxide In water for 36h;	53%
With water; potassium hydroxide at 0 - 20℃; for 32h;	50%
With potassium hydroxide In ethanol at 25℃; for 48h;
With potassium hydroxide
With potassium hydroxide at 20℃; for 72h;

(S)-(-)-β-methyl-β-propiolactone (65058-82-4) → (S)-3-Hydroxybutanoic Acid (6168-83-8) + (R)-3-Mercaptobuttersaeure (115395-16-9)

Conditions	Yield
With sodium hydrogensulfide In water 0 deg C, 1 h, then room temp., 24 h; Yields of byproduct given;	A n/a B 47%

3-hydroxybutanenitrile (4368-06-3) → (S)-3-Hydroxybutanoic Acid (6168-83-8)

Conditions	Yield
With Rhodococcus erythropolis SET1 cells In aq. phosphate buffer at 25℃; for 24h; pH=7; Microbiological reaction; enantioselective reaction;	42%
With hydrogenchloride
With bacterial isolate In aq. phosphate buffer at 15℃; pH=7.2;	n/a

1.3-butanediol (18826-95-4, 107-88-0) → 1,3-butanediol (24621-61-2) + (S)-3-Hydroxybutanoic Acid (6168-83-8)

Conditions	Yield
With phosphate buffer at 30℃; for 24h; Candida boidinii KK912 (IFO 10574);	A 32% B 13%

3-aminobutyric acid (2835-82-7) → (S)-3-Hydroxybutanoic Acid (6168-83-8)

Conditions	Yield
With cis-nitrous acid nachfolgend Verseifen;

methyl 3-aminobutyrate (6078-06-4) → (S)-3-Hydroxybutanoic Acid (6168-83-8)

Conditions	Yield
With cis-nitrous acid nachfolgend Verseifen;

acetaldol (107-89-1) → (S)-3-Hydroxybutanoic Acid (6168-83-8)

Conditions	Yield
bei der Einw. von Bact. ascendens;

2-acetoacetic acid (541-50-4) → (S)-3-Hydroxybutanoic Acid (6168-83-8)

Conditions	Yield
bei der Reduktion durch gaerende Hefe;
durch ein stereospezifisches Enzym aus Schweinenieren-Extrakt;

3-Hydroxybutyric acid (300-85-6, 625-71-8) → (S)-3-Hydroxybutanoic Acid (6168-83-8)

Conditions	Yield
Man laesst auf der Ammoniumsalzloesung Aspergillus griseus wachsen;

1.3-butanediol (18826-95-4, 107-88-0) → (S)-3-Hydroxybutanoic Acid (6168-83-8) + (R)-3-hydroxybutyric acid (625-72-9) + 2-acetoacetic acid (541-50-4)

Conditions	Yield
With D-glucose; calcium carbonate at 27℃; for 48h; Hansenula anomala IFO 0195; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With D-glucose; calcium carbonate at 27℃; for 48h; Product distribution; Hansenula anomala IFO 0195, potato-dextrose-agar; other yeasts, influence of glucose, fructose, temperature: stereoselectivity; also with optically active 1,3-butanediol;

2-acetoacetic acid (541-50-4) → (S)-3-Hydroxybutanoic Acid (6168-83-8) + (R)-3-hydroxybutyric acid (625-72-9)

Conditions	Yield
With potassium dihydrogenphosphate; baker's yeast; D-glucose In water at 28℃; for 9h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With potassium dihydrogenphosphate; baker's yeast; D-glucose In water at 28℃; for 9h; Product distribution; other times; other β-keto acids investigated;
With diisopinocampheylborane In tetrahydrofuran at 20℃; for 32h; Title compound not separated from byproducts.;

ethyl (S)-3-hydroxybutyrate (56816-01-4) → (S)-3-Hydroxybutanoic Acid (6168-83-8)

Conditions	Yield
With potassium hydroxide for 12h; Ambient temperature;
With Candida antarctica lipase B; 4-nitro-phenol; MOPS buffer In water at 25℃; pH=7.2; Enzyme kinetics; Further Variations:; Reagents; Enzymatic reaction;

ethyl acetoacetate (141-97-9) → (S)-3-Hydroxybutanoic Acid (6168-83-8) + (R)-3-hydroxybutyric acid (625-72-9) + Ethyl (R)-3-hydroxybutanoate (24915-95-5) + ethyl (S)-3-hydroxybutyrate (56816-01-4)

Conditions	Yield
With Halobacterium halobium; pepton; potassium chloride; water; sodium citrate; magnesium sulfate; sodium chloride at 40℃; for 120h; Irradiation; Yields of byproduct given. Title compound not separated from byproducts;
With Halobacterium halobium; pepton; potassium chloride; sodium citrate; magnesium sulfate; sodium chloride In water at 40℃; for 120h; Irradiation; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

(S)-(-)-2,3-Dihydro-2-methyl-4H-1-benzopyran-4-one (108379-02-8) → (S)-3-Hydroxybutanoic Acid (6168-83-8)

Conditions	Yield
With ozone In water; acetic acid for 2h;

1'(R),6-Dimethyl-4'(S)-isopropyl-4-oxospiro--dioxin> (105252-84-4) → (S)-3-Hydroxybutanoic Acid (6168-83-8)

Conditions	Yield
With hydrogen; platinum(IV) oxide In methanol Ambient temperature;

2-hydroxymuconate disodium salt → (S)-3-Hydroxybutanoic Acid (6168-83-8)

Conditions	Yield
With sodium dihydrogenphosphate; manganese(ll) chloride 1.) 4-oxalocrotonate tautomerase (4-OT), RT, 2 h, 2.) oxalocrotonate decarboxylase, vinylpyruvate hydratase, RT, 1.5 h; Multistep reaction;

l-menthyl (2S,6S)-6-methyl-4-oxo-1,3-dioxane-2-carboxylate → (S)-3-Hydroxybutanoic Acid (6168-83-8)

Conditions	Yield
With potassium hydroxide In methanol at 50℃; for 0.0833333h;

(S)-3-(benzyloxy)butanoic acid (182970-04-3) → (S)-3-Hydroxybutanoic Acid (6168-83-8)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethyl acetate for 5h;

(+-)-3-hydroxy-butyric acid → (S)-3-Hydroxybutanoic Acid (6168-83-8)

Conditions	Yield
With Quinine

potassium-salt of/the/ acetoacetic acid → (S)-3-Hydroxybutanoic Acid (6168-83-8)

Conditions	Yield
With Baecker-yeast

(S)-3-hydroxybutyric acid methyl ester (53562-86-0) → methanol (67-56-1) + (S)-3-Hydroxybutanoic Acid (6168-83-8)

Conditions	Yield
With 2-(di(2-hydroxyethyl)amino)ethanesulfonic acid; lipase from Ophiostoma piliferum In water at 25℃; pH=7.20; Enzyme kinetics;
With 2-(di(2-hydroxyethyl)amino)ethanesulfonic acid; lipase from Bacillus thermocatenulanatus In water at 40℃; pH=7.20; Enzyme kinetics;

ethyl (S)-3-hydroxybutyrate (56816-01-4) → ethanol (64-17-5) + (S)-3-Hydroxybutanoic Acid (6168-83-8)

Conditions	Yield
With 2-(di(2-hydroxyethyl)amino)ethanesulfonic acid; lipase from Ophiostoma piliferum In water at 25℃; pH=7.20; Enzyme kinetics;
With 2-(di(2-hydroxyethyl)amino)ethanesulfonic acid; lipase from Bacillus thermocatenulanatus In water at 40℃; pH=7.20; Enzyme kinetics;

6-Methyl-2-((1R,2S,3R,5R)-2,6,6-trimethyl-bicyclo[3.1.1]hept-3-yl)-[1,3,2]dioxaborinan-4-one → (S)-3-Hydroxybutanoic Acid (6168-83-8) + (R)-3-hydroxybutyric acid (625-72-9)

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide In tetrahydrofuran Title compound not separated from byproducts.;

(S)-3-hydroxybutyraldehyde (117706-98-6) → (S)-3-Hydroxybutanoic Acid (6168-83-8)

Conditions	Yield
With sodium chlorite

perennisaponin I (1190432-98-4) → (S)-3-Hydroxybutanoic Acid (6168-83-8) + polygalacic acid 3-(α-L-rhamnopyranoside) (121324-22-9) + acetic acid (64-19-7)

Conditions	Yield
With potassium hydroxide In 1,4-dioxane; water at 40℃; for 12h;	A n/a B 2 mg C n/a

perennisaponin J (1190433-12-5) → (S)-3-Hydroxybutanoic Acid (6168-83-8) + polygalacic acid 3-(α-L-rhamnopyranoside) (121324-22-9) + acetic acid (64-19-7)

Conditions	Yield
With potassium hydroxide In 1,4-dioxane; water at 40℃; for 12h;	A n/a B 2 mg C n/a

perennisaponin K (1190433-29-4) → (S)-3-Hydroxybutanoic Acid (6168-83-8) + polygalacic acid 3-(α-L-rhamnopyranoside) (121324-22-9) + acetic acid (64-19-7)

Conditions	Yield
With potassium hydroxide In 1,4-dioxane; water at 40℃; for 12h;	A n/a B 2 mg C n/a

perennisaponin L (1190433-46-5) → (S)-3-Hydroxybutanoic Acid (6168-83-8) + polygalacic acid 3-(α-L-rhamnopyranoside) (121324-22-9) + acetic acid (64-19-7)

Conditions	Yield
With potassium hydroxide In 1,4-dioxane; water at 40℃; for 12h;	A n/a B 2 mg C n/a

bortezomib (390800-88-1) + (S)-3-Hydroxybutanoic Acid (6168-83-8) → N-[(1S)-1-benzyl-2-({(1R)-3-methyl-1-[(4S)-4-methyl-6-oxo-1,3,2-dioxaborinan-2-yl]butyl}amino)-2-oxoethyl]pyrazine-2-carboxamide (1201902-96-6)

Conditions	Yield
In ethyl acetate at 25 - 60℃;	96%

(S)-3-Hydroxybutanoic Acid (6168-83-8) + Ν,Ν',Ν''-[boroxin-2,4,6-triyltris[[(1R)-3-methylbutane-1,1-diyl]imino(2-oxoethane-2,1-diyl)]]tris(2,5-dichlorobenzamide) (1201903-03-8) → 2,5-dichloro-N-[2-({(1R)-3-methyl-1-[(4S)-4-methyl-6-oxo-1,3,2-dioxaborinan-2-yl]butyl}amino)-2-oxoethyl]benzamide (1201902-87-5)

Conditions	Yield
In ethyl acetate at 25 - 60℃;	95%

(S)-3-Hydroxybutanoic Acid (6168-83-8) + benzyl alcohol (100-51-6) → 3-hydroxybutyric acid benzyl ester (127604-17-5)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In chloroform at 0℃; for 6h;	89%

(S)-3-Hydroxybutanoic Acid (6168-83-8) + 5-{9-isobutyl-6-[(3S)-3-methylmorpholin-4-yl]-8-piperazin-1-yl-9H-purin-2-yl}pyrimidin-2-amine (1222106-77-5) → (2S)-4-(4-{2-(2-Aminopyrimidin-5-yl)-9-isobutyl-6-[(3S)-3-methylmorpholin-4-yl]-9H-purin-8-yl}piperazin-1-yl)-4-oxobutan-2-ol (1222105-18-1)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 21h;	81%

(S)-3-Hydroxybutanoic Acid (6168-83-8) + 4-methoxy-aniline (104-94-9) → (S)-3-hydroxy-N-(4-methoxyphenyl)butanamide (127604-09-5)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 0 - 20℃; Inert atmosphere;	75%

ethanol (64-17-5) + (S)-3-Hydroxybutanoic Acid (6168-83-8) → ethyl (S)-3-hydroxybutyrate (56816-01-4)

Conditions	Yield
With sulfuric acid	73%
With sulfuric acid	73%

(S)-3-Hydroxybutanoic Acid (6168-83-8) + benzyl 2-amino-(R)-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside (195006-98-5) → benzyl (R)-4,6-O-benzylidene-2-deoxy-2-[(S)-3-hydroxybutanamido]-β-D-allopyranoside

Conditions	Yield
With 1-hydroxy-pyrrolidine-2,5-dione; triethylamine; dicyclohexyl-carbodiimide In 1,4-dioxane at 20℃;	72%

(S)-3-Hydroxybutanoic Acid (6168-83-8) + 3-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-5-(1-methyl-3-(piperidin-4-yl)-1H-1,2,4-triazol-5-yl)pyrazin-2-amine (1620576-76-2) → (3S)-1-[4-[5-[5-amino-6-(5-tert-butyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]-1-methyl-1,2,4-triazol-3-yl]-1-piperidyl]-3-hydroxy-butan-1-one (1620576-66-0)

Conditions	Yield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;	68%

(S)-3-Hydroxybutanoic Acid (6168-83-8) + (R)-N-(6-(1-(1-((tert-butyldimethylsilyl)oxy)propan-2-yl)-1H-tetrazol-5-yl)pyridin-2-yl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-7-carboxamide → 2-((S)-3-hydroxybutanoyl)-N-(6-(1-((R)-1-hydroxypropan-2-yl)-1H-tetrazol-5-yl)pyridin-2-yl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-7-carboxamide

Conditions

Yield

Stage #1: (S)-3-Hydroxybutanoic Acid; (R)-N-(6-(1-(1-((tert-butyldimethylsilyl)oxy)propan-2-yl)-1H-tetrazol-5-yl)pyridin-2-yl)-6-methoxy-1,2,3,4-tetrahydroisoquinoline-7-carboxamide With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 2h; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide at 20℃; for 1h;

66%

(S)-3-Hydroxybutanoic Acid (6168-83-8) + (S)-3-aminocaprolactam hydrochloride (26081-03-8, 26081-07-2, 29110-16-5, 29426-64-0, 40862-36-0) → (S)-3-[(S)-3-hydroxybutyramido]-hexahydro-2-azepinone

Conditions	Yield
With dmap; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;	62%

(S)-3-Hydroxybutanoic Acid (6168-83-8) + 5-{9-isobutyl-8-[(3R)-3-methylpiperazin-1-yl]-6-morpholin-4-yl-9H-purin-2-yl}pyrimidin-2-amine (1222104-29-1) → (2S)-4-{(2R)-4-[2-(2-Aminopyrimidin-5-yl)-9-isobutyl-6-morpholin-4-yl-9H-purin-8-yl]-2-methylpiperazin-1-yl}-4-oxobutan-2-ol (1222104-71-3)

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 40℃; for 16h;	61%

(S)-3-Hydroxybutanoic Acid (6168-83-8) + 5-(9-isobutyl-6-morpholin-4-yl-8-piperazin-1-yl-9H-purin-2-yl)pyrimidin-2-amine (1222105-31-8) → (2S)-4-{4-[2-(2-Aminopyrimidin-5-yl)-9-isobutyl-6-morpholin-4-yl-9H-purin-8-yl]piperazin-1-yl}-4-oxobutan-2-ol (1222104-67-7)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 16h;	56%

(S)-3-Hydroxybutanoic Acid (6168-83-8) + (3aS,6aR)-2-(1-(2-fluorophenyl)-1H-indazol-4-yl)hexahydropyrrolo[3,4-c]pyrrol-1(2H)-one → (3aS,6aR)-2-[1-(2-fluorophenyl)-1H-indazol-4-yl]-5-[(3S)-3-hydroxybutanoyl]hexahydropyrrolo[3,4-c]pyrrol-1(2H)-one

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In tetrahydrofuran at 20℃; for 3h;	53%

(S)-3-Hydroxybutanoic Acid (6168-83-8) + 5-[6-morpholin-4-yl-8-piperazin-1-yl-9-(2,2,2-trifluoroethyl)-9H-purin-2-yl]pyrimidin-2-amine trifluoroacetate → (2S)-4-{4-[2-(2-Aminopyrimidin-5-yl)-6-morpholin-4-yl-9-(2,2,2-trifluoroethyl)-9H-purin-8-yl]piperazin-1-yl}-4-oxobutan-2-ol (1222104-55-3)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide for 15h;	50%

(S)-3-Hydroxybutanoic Acid (6168-83-8) + pivalaldehyde (630-19-3) → (2S,6S)-2-tert-Butyl-6-methyl-[1,3]dioxan-4-one

Conditions	Yield
With Dowex 50W In dichloromethane Cyclization; Etherification; Heating;	48%

(S)-3-Hydroxybutanoic Acid (6168-83-8) + 5-{9-isobutyl-8-[(3S)-3-methylpiperazin-1-yl]-6-morpholin-4-yl-9H-purin-2-yl}pyrimidin-2-amine (1222104-28-0) → (2S)-4-{(2S)-4-[2-(2-Aminopyrimidin-5-yl)-9-isobutyl-6-morpholin-4-yl-9H-purin-8-yl]-2-methylpiperazin-1-yl}-4-oxobutan-2-ol (1222104-70-2)

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 40℃; for 16h;	48%

(S)-3-Hydroxybutanoic Acid (6168-83-8) + L-cysteine methyl ester hydrochloride (18598-63-5) → methyl (R)-2-((S)-3-hydroxybutyrylamino)-3-mercaptopropionate (676346-96-6)

Conditions	Yield
With 4-methyl-morpholine; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In acetonitrile at 0℃; for 3h;	42%

3-{[(R)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl]carbonylamino}-1-(2-mercaptoethylamino)-1-propanone (167308-64-7) + (S)-3-Hydroxybutanoic Acid (6168-83-8) → dibenzyl phosphochloridate (538-37-4)

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h;	40.56%

(S)-3-Hydroxybutanoic Acid (6168-83-8) + (3aR,6aS)-2-[1-(2-fluorophenyl)-1H-indazol-4-yl]hexahydropyrrolo[3,4-c]pyrrol-1(2H)-one → (3aR,6aS)-2-[1-(2-fluorophenyl)-1H-indazol-4-yl]-5-[(3S)-3-hydroxybutanoyl]hexahydropyrrolo[3,4-c]pyrrol-1(2H)-one

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In tetrahydrofuran at 20℃; for 16h;	40%

4-(4-aminophenyl)-N-(4-morpholin-4-ylphenyl)pyrimidin-2-amine + (S)-3-Hydroxybutanoic Acid (6168-83-8) → (S)-3-hydroxy-N-(4-(2-(4-{morpholinophenyl}amino)pyrimidin-4-yl)phenyl)butanamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 2h;	22%

(S)-3-Hydroxybutanoic Acid (6168-83-8) → (4S,8S,12S,16S,20S)-4,8,12,16,20-Pentamethyl-1,5,9,13,17-pentaoxa-cycloicosane-2,6,10,14,18-pentaone (116838-42-7) + (4S,8S,12S,16S,20S,24S)-4,8,12,16,20,24-Hexamethyl-1,5,9,13,17,21-hexaoxa-cyclotetracosane-2,6,10,14,18,22-hexaone (116838-43-8) + (4S,8S,12S,16S,20S,24S,28S)-4,8,12,16,20,24,28-Heptamethyl-1,5,9,13,17,21,25-heptaoxa-cyclooctacosane-2,6,10,14,18,22,26-heptaone (116838-44-9)

Conditions	Yield
With 2,4,6-trichlorobenzoyl chloride; triethylamine In tetrahydrofuran 1.) 0 deg C, 30 min, 2.) 0 deg C to room temperature, 1.5 h;	A 13% B 13% C 7%
With trichlorobenzoyl chloride; triethylamine In tetrahydrofuran 1.) 0 deg C, 30 min, 2.) 0 deg C to room temperature, 1.5 h;	A 13% B 13% C 7%
With 2,4,6-trichlorobenzoyl chloride; triethylamine In tetrahydrofuran 1.) 0 deg C, 30 min, 2.) 0 deg C to room temperature;	A 13% B 13% C 7%

diazomethane (186581-53-3, 908094-01-9) + (S)-3-Hydroxybutanoic Acid (6168-83-8) → (S)-3-hydroxybutyric acid methyl ester (53562-86-0)

Conditions	Yield
In diethyl ether	12%
With diethyl ether
In diethyl ether Yield given;
In diethyl ether for 0.166667h; Ambient temperature; Yield given;

Upstream product

• 4368-06-3 3-hydroxybutanenitrile 
• 2835-82-7 3-aminobutyric acid 
• 6078-06-4 methyl 3-aminobutyrate 
• 107-89-1 acetaldol 
• 541-50-4 2-acetoacetic acid 
• 300-85-6 3-Hydroxybutyric acid 
• 53562-86-0 (S)-3-hydroxybutyric acid methyl ester 
• 18826-95-4 1.3-butanediol 
• 56816-01-4 ethyl (S)-3-hydroxybutyrate 
• 141-97-9 ethyl acetoacetate 
• 108379-02-8 (S)-(-)-2,3-Dihydro-2-methyl-4H-1-benzopyran-4-one 
• 105252-84-4 1'(R),6-Dimethyl-4'(S)-isopropyl-4-oxospiro--dioxin> 
• 65058-82-4 (S)-(-)-β-methyl-β-propiolactone 
• 182970-04-3 (S)-3-(benzyloxy)butanoic acid 

Downstream Products

• 53562-86-0 (S)-3-hydroxybutyric acid methyl ester 
• 127604-17-5 3-hydroxybutyric acid benzyl ester 
• 107-93-7 (E)-but-2-enoic acid 
• 914491-24-0 C₁₂H₁₇NO₃ 
• 127604-09-5 (S)-3-hydroxy-N-(4-methoxyphenyl)butanamide 
• 220654-32-0 C₈H₁₅NO₃S 
• 56816-01-4 ethyl (S)-3-hydroxybutyrate 
• 538-37-4 dibenzyl phosphochloridate 
• 77629-24-4 O-benzylcobactin T 

Relevant articles and documents

SYNTHESIS OF 3-HYDROXYBUTYRYL 3-HYDROXYBUTYRATE AND RELATED COMPOUNDS

In various embodiments methods of preparing hydroxybutyryl 3-hydroxybutyrate and related compounds are provided along with methods of use thereof.

Process Optimisation Studies and Aminonitrile Substrate Evaluation of Rhodococcus erythropolis SET1, A Nitrile Hydrolyzing Bacterium

A comprehensive series of optimization studies including pH, solvent and temperature were completed on the nitrile hydrolyzing Rhodococcus erythropolis bacterium SET1 with the substrate 3-hydroxybutyronitrile. These identified temperature of 25 °C and pH of 7 as the best conditions to retain enantioselectivity and activity. The effect of the addition of organic solvents to the biotransformation mixture was also determined. The results of the study suggested that SET1 is suitable for use in selected organo-aqueous media at specific ratios only. The functional group tolerance of the isolate with unprotected and protected β-aminonitriles, structural analogues of β-hydroxynitriles was also investigated with disappointingly poor isolated yields and selectivity obtained. The isolate was further evaluated with the α- aminonitrile phenylglycinonitrile generating acid in excellent yield and ee (>99 % (S) – isomer and 50 % yield). A series of pH studies with this substrate indicated pH 7 to be the optimum pH to avoid product and substrate degradation.

Efficient synthesis of the ketone body ester (R)-3-hydroxybutyryl-(R)-3-hydroxybutyrate and its (S,S) enantiomer

The ketone body ester (R)-3-hydroxybutyryl-(R)-3-hydroxybutyrate and its (S,S) enantiomer were prepared in a short, operationally simple synthetic sequence from racemic β-butyrolactone. Enantioselective hydrolysis of β-butyrolactone with immobilized Candida antarctica lipase-B (CAL-B) results in (R)-β-butyrolactone and (S)-β-hydroxybutyric acid, which are easily converted to (R) or (S)-ethyl-3-hydroxybutyrate and reduced to (R) or (S)-1,3 butanediol. Either enantiomer of ethyl-3-hydroxybutyrate and 1,3 butanediol are then coupled, again using CAL-B, to produce the ketone body ester product. This is an efficient, scalable, atom-economic, chromatography-free, and low cost synthetic method to produce the ketone body esters.