(R)-3-Hydroxybutyric acid supplier

Name
(R)-3-HYDROXYBUTYRIC ACID
EINECS 210-909-6
CAS No. 625-72-9
Article Data75
CAS DataBase
Density 1.195 g/cm³
Solubility
Melting Point 49-50 °C(lit.)
Formula C₄H₈O₃
Boiling Point 269.216 °C at 760 mmHg
Molecular Weight 104.106
Flash Point 121.011 °C
Transport Information
Appearance white crystal
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Butanoicacid, 3-hydroxy-, (R)-;Butyric acid, 3-hydroxy-, D-(-)- (8CI);(-)-3-Hydroxy-n-butyric acid;(-)-3-Hydroxybutyric acid;(3R)-3-Hydroxybutyricacid;(R)-(-)-3-Hydroxybutyric acid;(R)-(-)-b-Hydroxybutyric acid;(R)-3-Hydroxybutanoic acid;(R)-3-Hydroxybutyric acid;(R)-b-Hydroxybutanoic acid;(R)-b-Hydroxybutyric acid;D-(-)-3-Hydroxybutanoic acid;D-(-)-3-Hydroxybutyric acid;D-(-)-b-Hydroxybutyric acid;D-3-Hydroxybutyric acid;
PSA 57.53000
LogP -0.15810

Synthetic route

: 3976-69-0
Methyl (R)-3-hydroxybutyrate

: 625-72-9
(R)-3-hydroxybutyric acid

Conditions

Conditions	Yield
Stage #1: Methyl (R)-3-hydroxybutyrate With potassium hydroxide In water at 0 - 20℃; for 48h; Inert atmosphere; Stage #2: With hydrogenchloride In water pH=1; Inert atmosphere;	94%
With potassium hydroxide In water at 4℃; for 480h;	91%
Stage #1: Methyl (R)-3-hydroxybutyrate With potassium hydroxide; water at 0℃; for 25.5h; Stage #2: With hydrogenchloride; water at 5℃;	87%

: 13613-65-5
sodium (R)-3-hydroxybutyrate

: 625-72-9
(R)-3-hydroxybutyric acid

Conditions

Conditions	Yield
With DOWEX 50x8-200 ion-exchange resin In methanol	94%
With hydrogenchloride; water pH=1;	69%
With hydrogenchloride; water

: 24915-95-5
Ethyl (R)-3-hydroxybutanoate

: 625-72-9
(R)-3-hydroxybutyric acid

Conditions

Conditions	Yield
With potassium hydroxide at 0℃; for 24h;	93%
With sodium hydroxide In water at 10℃; for 6h;	85%
With potassium hydroxide for 12h; Ambient temperature;

: 77877-38-4
(3'R,4S)-3-(3'-hydroxybutanoyl)-4-(1-methylethyl)-2-oxazolidinone

: 625-72-9
(R)-3-hydroxybutyric acid

Conditions

Conditions	Yield
With lithium hydroxide; dihydrogen peroxide In tetrahydrofuran at 20℃; for 1h;	62%
With potassium hydroxide In methanol at 0℃; for 0.75h;

poly<(R)-3-hydroxybutanoic acid>: poly<(R)-3-hydroxybutanoic acid>

: 625-72-9
(R)-3-hydroxybutyric acid

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In methanol; 1,2-dichloro-ethane for 15h; Heating;	54%

: 5405-41-4
ethyl 3-hydroxybutyrate

A: 625-72-9
(R)-3-hydroxybutyric acid

B: 56816-01-4
ethyl (S)-3-hydroxybutyrate

Conditions

Conditions	Yield
With sodium hydroxide In water at 30℃; pH=6.9;	A n/a B 36.4%

: 4368-06-3
3-hydroxybutanenitrile

: 625-72-9
(R)-3-hydroxybutyric acid

Conditions

Conditions	Yield
With hydrogenchloride

: 25139-77-9
(S)‐3‐chlorobutanoic acid

: 625-72-9
(R)-3-hydroxybutyric acid

Conditions

Conditions	Yield
With water

: 6078-06-4
methyl 3-aminobutyrate

: 625-72-9
(R)-3-hydroxybutyric acid

Conditions

Conditions	Yield
With cis-nitrous acid Verseifung des Reaktionsproduktes;

: 126575-28-8
(S)-3-chloro-butyric acid methyl ester; methyl ester of/the/ dextrorotatory β-chloro-butyric acid

: 625-72-9
(R)-3-hydroxybutyric acid

Conditions

Conditions	Yield
With water

: 52020-45-8
(R)-(-)-3-acetoxybutyric acid

: 625-72-9
(R)-3-hydroxybutyric acid

Conditions

Conditions	Yield
With potassium hydroxide

: 50-99-7
D-glucose

: 625-72-9
(R)-3-hydroxybutyric acid

Conditions

Conditions	Yield
Vergaerung auch von anderen Zuckern durch Bac.megatherium (oder andere Mikroorganismen, z.B.Bac.cereus, Bac.polymyxa) bei 30grad und Autolyse der entstandenen intracellulaeren Polysaeure;

: 541-50-4
2-acetoacetic acid

: 625-72-9
(R)-3-hydroxybutyric acid

Conditions

Conditions	Yield
bei der Durchstroemung der ueberlebenden Hundeleber;
in tierischen Geweben unter anaeroben Bedingungen;
With hydrogen in Gegenwart von zellfreies Enzymextrakt aus Clostridium kluyveri;

: 5699-58-1
2,4-dioxo-pentanoic acid

: 625-72-9
(R)-3-hydroxybutyric acid

Conditions

Conditions	Yield
in tierischen Geweben unter anaeroben Bedingungen;

: 3128-06-1
5-ketohexanoic acid

: 625-72-9
(R)-3-hydroxybutyric acid

Conditions

Conditions	Yield
bei der Leberdurchstroemung;

: 64-19-7
acetic acid

: 625-72-9
(R)-3-hydroxybutyric acid

Conditions

Conditions	Yield
bei der Leberdurchstroemung;

: 142-62-1
hexanoic acid

: 625-72-9
(R)-3-hydroxybutyric acid

Conditions

Conditions	Yield
bei der Leberdurchstroemung;

: 300-85-6, 625-71-8
3-Hydroxybutyric acid

: 625-72-9
(R)-3-hydroxybutyric acid

Conditions

Conditions	Yield
durch Pilze;

: 107-92-6
butyric acid

: 625-72-9
(R)-3-hydroxybutyric acid

Conditions

Conditions	Yield
bei der Leberdurchstroemung;

: 300-85-6, 625-71-8
3-Hydroxybutyric acid

: 130-95-0
Quinine

: 625-72-9
(R)-3-hydroxybutyric acid

: 1685-91-2
xanthomegnin

: 625-72-9
(R)-3-hydroxybutyric acid

Conditions

Conditions	Yield
Multistep reaction;

: 3-<2-Hydroxy-propyl>-2,6-bis-hydroxymethyl-anisol

: 625-72-9
(R)-3-hydroxybutyric acid

Conditions

Conditions	Yield
(i) O3, CHCl3, (ii) Ag2O, H2O; Multistep reaction;

: 5,5,7-OH(3)-Oct-2-enoic Saeure

: 625-72-9
(R)-3-hydroxybutyric acid

Conditions

Conditions	Yield
With sodium periodate

: 18826-95-4, 107-88-0
1.3-butanediol

A: 6168-83-8
(S)-3-Hydroxybutanoic Acid

B: 625-72-9
(R)-3-hydroxybutyric acid

C: 541-50-4
2-acetoacetic acid

Conditions

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;

...Expand

: 541-50-4
2-acetoacetic acid

A: 6168-83-8
(S)-3-Hydroxybutanoic Acid

B: 625-72-9
(R)-3-hydroxybutyric acid

Conditions

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.;

: 141-97-9
ethyl acetoacetate

A: 6168-83-8
(S)-3-Hydroxybutanoic Acid

B: 625-72-9
(R)-3-hydroxybutyric acid

C: 24915-95-5
Ethyl (R)-3-hydroxybutanoate

D: 56816-01-4
ethyl (S)-3-hydroxybutyrate

Conditions

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;

...Expand

: 114701-16-5, 114761-10-3
(4R,6S,7S,10R)-7-Isopropyl-4,10-dimethyl-1,5-dioxa-spiro[5.5]undecan-2-one

: 625-72-9
(R)-3-hydroxybutyric acid

Conditions

Conditions	Yield
With hydrogenchloride In diethyl ether Ambient temperature;

: 114592-78-8
(R)-3-Acetoxybuttersaeure-ethylester

: 625-72-9
(R)-3-hydroxybutyric acid

Conditions

Conditions	Yield
With sodium hydroxide; water 1.) room temp., 2 d; 2.) 4 deg C, 1 d; Yield given. Multistep reaction;

: l-menthyl (2R,6R)-2,6-dimethyl-4-oxo-1,3-dioxane-2-carboxylate

: 625-72-9
(R)-3-hydroxybutyric acid

Conditions

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

: 186581-53-3, 908094-01-9
diazomethane

: 625-72-9
(R)-3-hydroxybutyric acid

: 3976-69-0
Methyl (R)-3-hydroxybutyrate

Conditions

Conditions	Yield
In diethyl ether	100%
In methanol; diethyl ether at -10℃;	76%

: 625-72-9
(R)-3-hydroxybutyric acid

: 18162-48-6
tert-butyldimethylsilyl chloride

: 105729-41-7, 107493-76-5, 101515-46-2
3-(R)-t-butyldimethylsilyloxybutanoic acid

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 48h; Inert atmosphere;	100%
With dmap; triethylamine In dichloromethane for 36h; Ambient temperature;	84%

: 625-72-9
(R)-3-hydroxybutyric acid

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 126249-06-7, 122358-09-2
methyl 3(R)-<oxy>butanoate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h;	100%

: 625-72-9
(R)-3-hydroxybutyric acid

: 116-11-0
2-Methoxypropene

: 2,2,6-trimethyl-1,3-dioxane-4-one

Conditions

Conditions	Yield
Stage #1: (R)-3-hydroxybutyric acid In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: 2-Methoxypropene With Amberlyst 15H In dichloromethane at 20℃; for 2h; Inert atmosphere;	98.8%

: 75-77-4
chloro-trimethyl-silane

: 625-72-9
(R)-3-hydroxybutyric acid

: 108438-96-6
trimethylsilyl (R)-3-<(trimethylsilyl)oxy>butyrate

Conditions

Conditions	Yield
With triethylamine In dichloromethane for 48h; Ambient temperature;	94%
In tetrahydrofuran Heating;

: 625-72-9
(R)-3-hydroxybutyric acid

: 77611-42-8
L-α-amino-N-(benzyloxy)caprolactam

: 77629-24-4
benzyl cobactin T

Conditions

Conditions	Yield
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In tetrahydrofuran at 50℃; for 22h;	79%

: 625-72-9
(R)-3-hydroxybutyric acid

: 107-18-6
allyl alcohol

: 152996-89-9
(R)-3-hydroxybutanoic acid allylester

Conditions

Conditions	Yield
With sulfuric acid In benzene for 4h; Heating;	74%

: 625-72-9
(R)-3-hydroxybutyric acid

: 124-13-0
Octanal

: 99902-24-6
(2R,6R)-2-heptyl-6-methyl-1,3-dioxan-4-on

Conditions

Conditions	Yield
With Dowex 50*8; pyridinium p-toluenesulfonate In dichloromethane Heating;	71%

: 625-72-9
(R)-3-hydroxybutyric acid

: 124-13-0
Octanal

A: 99902-24-6
(2R,6R)-2-heptyl-6-methyl-1,3-dioxan-4-on

B: 99902-24-6
(2S,6R)-2-Heptyl-6-methyl-[1,3]dioxan-4-one

Conditions

Conditions	Yield
With pyridinium p-toluenesulfonate In dichloromethane Yields of byproduct given;	A 71% B n/a

...Expand

: 625-72-9
(R)-3-hydroxybutyric acid

: 100-51-6
benzyl alcohol

: 88280-53-9
(R)-3-hydroxybutanoic benzyl ester

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In benzene Heating;	71%

: 957208-91-2
C25H26N2O2

: 625-72-9
(R)-3-hydroxybutyric acid

: 957208-92-3
C29H32N2O4

Conditions

Conditions	Yield
With 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In chloroform at 20℃; for 1h;	70%

: 625-72-9
(R)-3-hydroxybutyric acid

: 81445-44-5
(S)-2-(benzyloxy)propanal

: 127680-52-8
(2R,6R)-2-<1-(S)-benzyloxyethyl>-6-methyl-1,3-dioxan-4-one

Conditions

Conditions	Yield
With pyridinium p-toluenesulfonate In dichloromethane Heating;	69%

: 104-53-0
3-phenyl-propionaldehyde

: 625-72-9
(R)-3-hydroxybutyric acid

: 99902-26-8
(2R,6R)-6-methyl-2-(2'-phenylethyl)-1,3-dioxan-4-on

Conditions

Conditions	Yield
With Dowex 50*8; pyridinium p-toluenesulfonate In dichloromethane Heating;	66%
With pyridinium p-toluenesulfonate In dichloromethane Heating;

: 104-53-0
3-phenyl-propionaldehyde

: 625-72-9
(R)-3-hydroxybutyric acid

A: 99902-26-8
(2R,6R)-6-methyl-2-(2'-phenylethyl)-1,3-dioxan-4-on

B: 112463-39-5
(2S,6R)-6-Methyl-2-phenethyl-[1,3]dioxan-4-one

Conditions

Conditions	Yield
With pyridinium p-toluenesulfonate In dichloromethane Yields of byproduct given;	A 66% B n/a

...Expand

: 124-19-6
nonan-1-al

: 625-72-9
(R)-3-hydroxybutyric acid

A: 99902-25-7
(2R,6R)-6-methyl-2-octyl-1,3-dioxan-4-on

B: 112463-27-1
(2S,6R)-6-methyl-2-octyl-1,3-dioxan-4-on

Conditions

Conditions	Yield
With Dowex 50*8; pyridinium p-toluenesulfonate In dichloromethane Heating;	A 66% B n/a
With pyridinium p-toluenesulfonate In dichloromethane Yield given. Yields of byproduct given. Title compound not separated from byproducts;

...Expand

: 625-72-9
(R)-3-hydroxybutyric acid

: 5-[1-(2-fluorophenyl)-1H-indazol-4-yl]hexahydropyrrolo[3,4-b]pyrrol-6-(1H)-one

: (3aR,6aR)-5-[1-(2-fluorophenyl)-1H-indazol-4-yl]-1-[(3R)-3-hydroxybutanoyl]hexahydropyrrolo[3,4-b]pyrrol-6(1H)-one

Conditions

Conditions	Yield
With triethylamine; 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 40℃; for 1h;	65%

: 625-72-9
(R)-3-hydroxybutyric acid

: 171287-62-0
[(S)-1-(tert-Butyl-diphenyl-silanyloxy)-2-oxo-azepan-3-yl]-carbamic acid benzyl ester

: 171287-63-1
(R)-N-[(S)-1-(tert-Butyl-diphenyl-silanyloxy)-2-oxo-azepan-3-yl]-3-hydroxy-butyramide

Conditions

Conditions	Yield
With dmap; 4-(dimethylamino)pyridine hydrochloride; dicyclohexyl-carbodiimide In chloroform at 40℃; for 0.5h;	63%

: 1007123-23-0
(S)-3-amino-1-(benzyloxy)azepan-2-one hydrobromide

: 625-72-9
(R)-3-hydroxybutyric acid

: 77629-24-4
benzyl cobactin T

Conditions

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In acetonitrile at 22℃; for 25h; Inert atmosphere;	62%

: 625-72-9
(R)-3-hydroxybutyric acid

: 78-84-2
isobutyraldehyde

A: 100017-85-4
(2R,6R)-2-isopropyl-6-methyl-1,3-dioxan-4-on

B: 112530-85-5
(2S,6R)-2-isopropyl-6-methyl-1,3-dioxan-4-on

Conditions

Conditions	Yield
With pyridinium p-toluenesulfonate In benzene Yields of byproduct given;	A 61% B n/a
With Amberlyst; Dowex 50*8; pyridinium p-toluenesulfonate In benzene Heating;	A 61% B n/a

...Expand

(R)-3-Hydroxybutyric acid Specification

The (R)-3-Hydroxybutyric acid is an organic compound with the formula C₄H₈O₃. The IUPAC name of this chemical is (3R)-3-hydroxybutanoic acid. With the CAS registry number 625-72-9, it is also named as 3-Hydroxybutanoic acid. The product's categories are Carboxylic Acids; Chiral Building Blocks; Organic Building Blocks.

Physical properties about (R)-3-Hydroxybutyric acid are: (1)ACD/BCF (pH 5.5): 1; (2)ACD/BCF (pH 7.4): 1; (3)ACD/KOC (pH 5.5): 1; (4)ACD/KOC (pH 7.4): 1; (5)#H bond acceptors: 3; (6)#H bond donors: 2; (7)#Freely Rotating Bonds: 3; (8)Polar Surface Area: 57.53 Å²; (9)Index of Refraction: 1.455; (10)Molar Refractivity: 23.638 cm³; (11)Molar Volume: 87.071 cm³; (12)Polarizability: 9.371×10^-24cm³; (13)Surface Tension: 46.362 dyne/cm; (14)Density: 1.196 g/cm³; (15)Flash Point: 121.011 °C; (16)Enthalpy of Vaporization: 58.908 kJ/mol; (17)Boiling Point: 269.216 °C at 760 mmHg; (18)Vapour Pressure: 0.001 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: CC(CC(=O)O)O
(2)InChI: InChI=1/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)
(3)InChIKey: WHBMMWSBFZVSSR-UHFFFAOYAO
(4)Std. InChI: InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)
(5)Std. InChIKey: WHBMMWSBFZVSSR-UHFFFAOYSA-N

Product Name

(R)-3-HYDROXYBUTYRIC ACID

Synthetic route

(R)-3-Hydroxybutyric acid Specification

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