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(R)-3-HYDROXYBUTYRIC ACID, also known as the R-enantiomer of 3-hydroxybutyric acid, is a vital compound involved in the synthesis and degradation of ketone bodies. It serves as an alternative energy source for the brain during hypoglycaemia and is also utilized in the production of biodegradable plastics.

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  • 625-72-9 Structure
  • Basic information

    1. Product Name: (R)-3-HYDROXYBUTYRIC ACID
    2. Synonyms: (R)-(-)-3-HYDROXYBUTYRIC ACID;(R)-3-HYDROXYBUTYRIC ACID;d-beta-hydroxybutyrate;(R)-3-Hydroxybutyrate;D-(-)-3-Hydroxybutyrate;D(-)-3-Hydroxybutyrate;D-3-Hydroxybutyric acid;(R)-3-Hydroxybutanoic acid
    3. CAS NO:625-72-9
    4. Molecular Formula: C4H8O3
    5. Molecular Weight: 104.1
    6. EINECS: 210-909-6
    7. Product Categories: Carboxylic Acids;Chiral Building Blocks;Organic Building Blocks
    8. Mol File: 625-72-9.mol
  • Chemical Properties

    1. Melting Point: 49-50 °C(lit.)
    2. Boiling Point: 269.216 °C at 760 mmHg
    3. Flash Point: 112 °C
    4. Appearance: white crystal
    5. Density: 1.195 g/cm3
    6. Vapor Pressure: 0.000979mmHg at 25°C
    7. Refractive Index: 1.455
    8. Storage Temp.: 2-8°C
    9. Solubility: N/A
    10. PKA: 4.36±0.10(Predicted)
    11. BRN: 1720568
    12. CAS DataBase Reference: (R)-3-HYDROXYBUTYRIC ACID(CAS DataBase Reference)
    13. NIST Chemistry Reference: (R)-3-HYDROXYBUTYRIC ACID(625-72-9)
    14. EPA Substance Registry System: (R)-3-HYDROXYBUTYRIC ACID(625-72-9)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26-36
    4. WGK Germany: 3
    5. RTECS:
    6. F: 3-10
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 625-72-9(Hazardous Substances Data)

625-72-9 Usage

Uses

Used in Pharmaceutical Industry:
(R)-3-HYDROXYBUTYRIC ACID is used as an energy source for the brain during [application reason] hypoglycaemia, providing a crucial alternative when glucose levels are low.
Used in Biodegradable Plastics Industry:
(R)-3-HYDROXYBUTYRIC ACID is used as a key component in the synthesis of [application type] biodegradable plastics, contributing to the development of environmentally friendly materials.

Check Digit Verification of cas no

The CAS Registry Mumber 625-72-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,2 and 5 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 625-72:
(5*6)+(4*2)+(3*5)+(2*7)+(1*2)=69
69 % 10 = 9
So 625-72-9 is a valid CAS Registry Number.
InChI:InChI=1/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m1/s1

625-72-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name (R)-3-hydroxybutyric acid

1.2 Other means of identification

Product number -
Other names (R)-3-HYDROXYBUTYRIC ACID

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:625-72-9 SDS

625-72-9Synthetic route

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

Methyl (R)-3-hydroxybutyrate

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

(R)-3-hydroxybutyric acid

Conditions
ConditionsYield
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%
sodium (R)-3-hydroxybutyrate
13613-65-5

sodium (R)-3-hydroxybutyrate

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

(R)-3-hydroxybutyric acid

Conditions
ConditionsYield
With DOWEX 50x8-200 ion-exchange resin In methanol94%
With hydrogenchloride; water pH=1;69%
With hydrogenchloride; water
Ethyl (R)-3-hydroxybutanoate
24915-95-5

Ethyl (R)-3-hydroxybutanoate

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

(R)-3-hydroxybutyric acid

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

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

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

(R)-3-hydroxybutyric acid

Conditions
ConditionsYield
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>

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

(R)-3-hydroxybutyric acid

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol; 1,2-dichloro-ethane for 15h; Heating;54%
ethyl 3-hydroxybutyrate
5405-41-4

ethyl 3-hydroxybutyrate

A

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

(R)-3-hydroxybutyric acid

B

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

ethyl (S)-3-hydroxybutyrate

Conditions
ConditionsYield
With sodium hydroxide In water at 30℃; pH=6.9;A n/a
B 36.4%
3-hydroxybutanenitrile
4368-06-3

3-hydroxybutanenitrile

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

(R)-3-hydroxybutyric acid

Conditions
ConditionsYield
With hydrogenchloride
(S)‐3‐chlorobutanoic acid
25139-77-9

(S)‐3‐chlorobutanoic acid

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

(R)-3-hydroxybutyric acid

Conditions
ConditionsYield
With water
methyl 3-aminobutyrate
6078-06-4

methyl 3-aminobutyrate

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

(R)-3-hydroxybutyric acid

Conditions
ConditionsYield
With cis-nitrous acid Verseifung des Reaktionsproduktes;
(S)-3-chloro-butyric acid methyl ester; methyl ester of/the/ dextrorotatory β-chloro-butyric acid
126575-28-8

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

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

(R)-3-hydroxybutyric acid

Conditions
ConditionsYield
With water
(R)-(-)-3-acetoxybutyric acid
52020-45-8

(R)-(-)-3-acetoxybutyric acid

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

(R)-3-hydroxybutyric acid

Conditions
ConditionsYield
With potassium hydroxide
D-glucose
50-99-7

D-glucose

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

(R)-3-hydroxybutyric acid

Conditions
ConditionsYield
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;
2-acetoacetic acid
541-50-4

2-acetoacetic acid

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

(R)-3-hydroxybutyric acid

Conditions
ConditionsYield
bei der Durchstroemung der ueberlebenden Hundeleber;
in tierischen Geweben unter anaeroben Bedingungen;
With hydrogen in Gegenwart von zellfreies Enzymextrakt aus Clostridium kluyveri;
2,4-dioxo-pentanoic acid
5699-58-1

2,4-dioxo-pentanoic acid

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

(R)-3-hydroxybutyric acid

Conditions
ConditionsYield
in tierischen Geweben unter anaeroben Bedingungen;
5-ketohexanoic acid
3128-06-1

5-ketohexanoic acid

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

(R)-3-hydroxybutyric acid

Conditions
ConditionsYield
bei der Leberdurchstroemung;
acetic acid
64-19-7

acetic acid

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

(R)-3-hydroxybutyric acid

Conditions
ConditionsYield
bei der Leberdurchstroemung;
hexanoic acid
142-62-1

hexanoic acid

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

(R)-3-hydroxybutyric acid

Conditions
ConditionsYield
bei der Leberdurchstroemung;
3-Hydroxybutyric acid
300-85-6, 625-71-8

3-Hydroxybutyric acid

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

(R)-3-hydroxybutyric acid

Conditions
ConditionsYield
durch Pilze;
butyric acid
107-92-6

butyric acid

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

(R)-3-hydroxybutyric acid

Conditions
ConditionsYield
bei der Leberdurchstroemung;
3-Hydroxybutyric acid
300-85-6, 625-71-8

3-Hydroxybutyric acid

Quinine
130-95-0

Quinine

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

(R)-3-hydroxybutyric acid

xanthomegnin
1685-91-2

xanthomegnin

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

(R)-3-hydroxybutyric acid

Conditions
ConditionsYield
Multistep reaction;
3-<2-Hydroxy-propyl>-2,6-bis-hydroxymethyl-anisol

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

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

(R)-3-hydroxybutyric acid

Conditions
ConditionsYield
(i) O3, CHCl3, (ii) Ag2O, H2O; Multistep reaction;
5,5,7-OH(3)-Oct-2-enoic Saeure

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

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

(R)-3-hydroxybutyric acid

Conditions
ConditionsYield
With sodium periodate
1.3-butanediol
18826-95-4, 107-88-0

1.3-butanediol

A

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

(S)-3-Hydroxybutanoic Acid

B

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

(R)-3-hydroxybutyric acid

C

2-acetoacetic acid
541-50-4

2-acetoacetic acid

Conditions
ConditionsYield
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

2-acetoacetic acid

A

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

(S)-3-Hydroxybutanoic Acid

B

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

(R)-3-hydroxybutyric acid

Conditions
ConditionsYield
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 acetoacetate
141-97-9

ethyl acetoacetate

A

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

(S)-3-Hydroxybutanoic Acid

B

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

(R)-3-hydroxybutyric acid

C

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

Ethyl (R)-3-hydroxybutanoate

D

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

ethyl (S)-3-hydroxybutyrate

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

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

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

(R)-3-hydroxybutyric acid

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether Ambient temperature;
(R)-3-Acetoxybuttersaeure-ethylester
114592-78-8

(R)-3-Acetoxybuttersaeure-ethylester

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

(R)-3-hydroxybutyric acid

Conditions
ConditionsYield
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

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

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

(R)-3-hydroxybutyric acid

Conditions
ConditionsYield
With potassium hydroxide In methanol at 50℃; for 0.0833333h;
(R)-3-hydroxybutyric acid
625-72-9

(R)-3-hydroxybutyric acid

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

Methyl (R)-3-hydroxybutyrate

Conditions
ConditionsYield
In diethyl ether100%
In methanol; diethyl ether at -10℃;76%
(R)-3-hydroxybutyric acid
625-72-9

(R)-3-hydroxybutyric acid

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

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

3-(R)-t-butyldimethylsilyloxybutanoic acid

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 48h; Inert atmosphere;100%
With dmap; triethylamine In dichloromethane for 36h; Ambient temperature;84%
(R)-3-hydroxybutyric acid
625-72-9

(R)-3-hydroxybutyric acid

triisopropylsilyl trifluoromethanesulfonate
80522-42-5

triisopropylsilyl trifluoromethanesulfonate

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

methyl 3(R)-butanoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h;100%
(R)-3-hydroxybutyric acid
625-72-9

(R)-3-hydroxybutyric acid

2-Methoxypropene
116-11-0

2-Methoxypropene

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

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

Conditions
ConditionsYield
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%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

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

(R)-3-hydroxybutyric acid

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

trimethylsilyl (R)-3-<(trimethylsilyl)oxy>butyrate

Conditions
ConditionsYield
With triethylamine In dichloromethane for 48h; Ambient temperature;94%
In tetrahydrofuran Heating;
(R)-3-hydroxybutyric acid
625-72-9

(R)-3-hydroxybutyric acid

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

L-α-amino-N-(benzyloxy)caprolactam

benzyl cobactin T
77629-24-4

benzyl cobactin T

Conditions
ConditionsYield
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In tetrahydrofuran at 50℃; for 22h;79%
(R)-3-hydroxybutyric acid
625-72-9

(R)-3-hydroxybutyric acid

allyl alcohol
107-18-6

allyl alcohol

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

(R)-3-hydroxybutanoic acid allylester

Conditions
ConditionsYield
With sulfuric acid In benzene for 4h; Heating;74%
(R)-3-hydroxybutyric acid
625-72-9

(R)-3-hydroxybutyric acid

Octanal
124-13-0

Octanal

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

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

Conditions
ConditionsYield
With Dowex 50*8; pyridinium p-toluenesulfonate In dichloromethane Heating;71%
(R)-3-hydroxybutyric acid
625-72-9

(R)-3-hydroxybutyric acid

Octanal
124-13-0

Octanal

A

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

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

B

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

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

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dichloromethane Yields of byproduct given;A 71%
B n/a
(R)-3-hydroxybutyric acid
625-72-9

(R)-3-hydroxybutyric acid

benzyl alcohol
100-51-6

benzyl alcohol

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

(R)-3-hydroxybutanoic benzyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene Heating;71%
C25H26N2O2
957208-91-2

C25H26N2O2

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

(R)-3-hydroxybutyric acid

C29H32N2O4
957208-92-3

C29H32N2O4

Conditions
ConditionsYield
With 4-methyl-morpholine; 1-hydroxy-7-aza-benzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In chloroform at 20℃; for 1h;70%
(R)-3-hydroxybutyric acid
625-72-9

(R)-3-hydroxybutyric acid

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

(S)-2-(benzyloxy)propanal

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

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

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dichloromethane Heating;69%
3-phenyl-propionaldehyde
104-53-0

3-phenyl-propionaldehyde

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

(R)-3-hydroxybutyric acid

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

(2R,6R)-6-methyl-2-(2'-phenylethyl)-1,3-dioxan-4-on

Conditions
ConditionsYield
With Dowex 50*8; pyridinium p-toluenesulfonate In dichloromethane Heating;66%
With pyridinium p-toluenesulfonate In dichloromethane Heating;
3-phenyl-propionaldehyde
104-53-0

3-phenyl-propionaldehyde

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

(R)-3-hydroxybutyric acid

A

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

(2R,6R)-6-methyl-2-(2'-phenylethyl)-1,3-dioxan-4-on

B

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

(2S,6R)-6-Methyl-2-phenethyl-[1,3]dioxan-4-one

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dichloromethane Yields of byproduct given;A 66%
B n/a
nonan-1-al
124-19-6

nonan-1-al

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

(R)-3-hydroxybutyric acid

A

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

(2R,6R)-6-methyl-2-octyl-1,3-dioxan-4-on

B

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

(2S,6R)-6-methyl-2-octyl-1,3-dioxan-4-on

Conditions
ConditionsYield
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;
(R)-3-hydroxybutyric acid
625-72-9

(R)-3-hydroxybutyric acid

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

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

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

Conditions
ConditionsYield
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%
(R)-3-hydroxybutyric acid
625-72-9

(R)-3-hydroxybutyric acid

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

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

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

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

Conditions
ConditionsYield
With dmap; 4-(dimethylamino)pyridine hydrochloride; dicyclohexyl-carbodiimide In chloroform at 40℃; for 0.5h;63%
(S)-3-amino-1-(benzyloxy)azepan-2-one hydrobromide
1007123-23-0

(S)-3-amino-1-(benzyloxy)azepan-2-one hydrobromide

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

(R)-3-hydroxybutyric acid

benzyl cobactin T
77629-24-4

benzyl cobactin T

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In acetonitrile at 22℃; for 25h; Inert atmosphere;62%
(R)-3-hydroxybutyric acid
625-72-9

(R)-3-hydroxybutyric acid

isobutyraldehyde
78-84-2

isobutyraldehyde

A

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

(2R,6R)-2-isopropyl-6-methyl-1,3-dioxan-4-on

B

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

(2S,6R)-2-isopropyl-6-methyl-1,3-dioxan-4-on

Conditions
ConditionsYield
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

625-72-9Relevant articles and documents

PANTETHEINE DERIVATIVES AND USES THEREOF

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Paragraph 2121, (2020/06/19)

The present disclosure relates to compounds of Formula (I), (II), or (II'): (I), (II), (II'), and pharmaceutically acceptable salts or solvates thereof. The present disclosure also relates to pharmaceutical compositions comprising the compounds and therapeutic and diagnostic uses of the compounds and pharmaceutical compositions.

Hansforesters A-M, polyesters from the sponge-associated fungus Hansfordia sinuosae with antibacterial activities

Wu, Zehong,Liu, Dong,Huang, Jian,Proksch, Peter,Zhu, Kui,Lin, Wenhan

, p. 39756 - 39768 (2018/12/13)

Bioassay-guided fractionation and chromatographic separation of a sponge-derived fungus Hansfordia sinuosae, resulted in the isolation of thirteen new polyesters namely hansforesters A-M (1-13), along with five known analogues involving ascotrichalactone A, ascotrichester B, 15G256π, 6R-hydroxymellein, and (?)orthosporin. The structures of the new compounds were determined through extensive spectroscopic analysis, in addition to the chemical conversion for the configurational assignment. The polyesters incorporating the motifs of orsellinic acid, 2,4-dihydroxy-6-acetonylbenzoic acid, and orcinotriol were found from nature for the first time. Hansforester A (1) and ascotrichalactone A exhibited potent inhibition against a panel of bacterial strains, including the agricultural pathogenic bacteria, Pseudomonas lachrymans, Agrobacterium tumefaciens, Xanthomonas vesicatoria, and Ralstonia solanacearum, with the MIC values of 15.6 μM, and the human infected bacterium Staphylococcus aureus with the MIC values of 3.9 μM. These findings suggested that hansforester A and ascotrichalactone A are the potential leads to be developed as the antibacterial agents for the treatment of agriculture bacterial pathogens.

Synthesis process of (R)-3-hydroxybutyric acid and salts thereof

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Paragraph 0048; 0049, (2017/10/07)

The invention discloses a synthesis process for preparing (R)-3-hydroxybutyric acid and sodium salt, potassium salt, magnesium salt and calcium salt thereof. The process includes steps: adding 3-oxobutanoate and a ruthenium complex catalyst into organic solvent according to a mole ratio of 1:0.0005-0.005, and reacting at 20-80 DEG C for 12-24h under a hydrogen pressure of 1-20bar to obtain (R)-3-hydroxybutyrate; dissolving (R)-3-hydroxybutyrate into water, and subjecting to reaction with sodium hydroxide, potassium hydroxide or calcium hydroxide for 2-12h at a low temperature to obtain sodium salt, potassium salt, magnesium salt and calcium salt of (R)-3-hydroxybutyric acid; subjecting water solution of (R)-3-sodium hydroxybutyrate to 732 cation exchange resin treatment to remove sodium ions to obtain (R)-3-hydroxybutyric acid; subjecting (R)-3-hydroxybutyric acid to reaction with magnesium hydroxide to obtain (R)-3-magnesium hydroxybutyrate. Ee values of (R)-3-hydroxybutyric acid and sodium salt, potassium salt, magnesium salt and calcium salt thereof reach 90% or above. The method has advantages of low environment pollution, low cost and easiness in aftertreatment.

Novel urushiols with human immunodeficiency virus type 1 reverse transcriptase inhibitory activity from the leaves of Rhus verniciflua

Kadokura, Kazunari,Suruga, Kohei,Tomita, Tsuyoshi,Hiruma, Wataru,Yamada, Motoyuki,Kobayashi, Akio,Takatsuki, Akira,Nishio, Toshiyuki,Oku, Tadatake,Sekino, Yoshihiro

, p. 148 - 153 (2015/02/19)

Two novel urushiols, 1 and 2, and two known urushiols, 3 and 4, were isolated from the leaves of Rhus verniciflua and were examined for their human immunodeficiency virus type 1 (HIV-1) reverse transcriptase (RT) inhibitory activity. The novel urushiols were found to be 1,2-dihydroxyphenyl-3-[7(E),9(Z),11(Z)-pentadecatrienyl]-14-ol (1) and 1,2-dihydroxyphenyl-3-[8(Z),10(E),12(E)-pentadecatrienyl]-14-ol (2) by spectroscopic analyses. The absolute configuration at C-14 in 1 and 2 was determined to be a racemic mixture of (R) and (S) isomers by ozonolysis. Compound 2 (IC50: 12.6 μM) showed the highest HIV-1 RT inhibitory activity among the four urushiols, being 2.5-fold more potent than the positive control, adriamycin (IC50: 31.9 μM). Although the known urushiols were isolated from the sap and leaves of R. verniciflua, 1 was exclusively present in the leaves, and higher amounts of 2 were found in the leaves than in the sap. Present findings indicate that the leaves of R. verniciflua represent a new biological resource from which novel and known urushiols may be prepared, and the possible use of novel urushiols as bioactive products.

A high throughput screening strategy for the assessment of nitrile-hydrolyzing activity towards the production of enantiopure β-hydroxy acids

Coady, Tracey M.,Coffey, Lee V.,O'Reilly, Catherine,Owens, Erica B.,Lennon, Claire M.

, p. 150 - 155 (2013/10/01)

Nitrile hydrolysing enzymes have found wide use in the pharmaceutical industry for the production of fine chemicals. This work presents a strategy that facilitates the rapid identification of bacterial isolates demonstrating nitrile hydrolysing activity. The strategy incorporates toxicity, starvation and induction studies along with subsequent colorimetric screening for activity, further focusing the assessment towards the substrates of interest. This high-throughput strategy uses a 96 well plate system, and has enabled the rapid biocatalytic screening of 256 novel bacterial isolates towards β-hydroxynitriles. Results demonstrate the strategy's potential to rapidly assess a variety of β-hydroxynitriles including aliphatic, aromatic and dinitriles. A whole cell catalyst Rhodococcus erythropolis SET1 was identified and found to catalyse the hydrolysis of 3-hydroxybutyronitrile with remarkably high enantioselectivity under mild conditions, to afford (S)-3-hydroxybutyric acid in 42% yield and >99.9% ee. The biocatalytic capability of this strain including the variation of parameters such as temperature and time were further investigated and all results indicate the presence of a highly enantioselective if not enantiospecific nitrilase enzyme within the microbial whole cell.

Syntheses of mycobactin analogs as potent and selective inhibitors of Mycobacterium tuberculosis

Juárez-Hernández, Raúl E.,Franzblau, Scott G.,Miller, Marvin J.

, p. 7584 - 7593 (2012/10/29)

Three analogs of mycobactin T, the siderophore secreted by Mycobacterium tuberculosis (Mtb) were synthesized and screened for their antibiotic activity against Mtb H37Rv and a broad panel of Gram-positive and Gram-negative bacteria. The synthetic mycobactins were potent (MIC90 0.02-0.88 μM in 7H12 media) and selective Mtb inhibitors, with no inhibitory activity observed against any other of the microorganisms tested. The maleimide-containing analog 40 represents a versatile platform for the development of mycobactin-drug conjugates, as well as other applications.

Total syntheses of the gregatins A-D and aspertetronin A: Structure revisions of these compounds and of aspertetronin B, together with plausible structure revisions of gregatin E, cyclogregatin, graminin A, the penicilliols A and B, and the huaspenones A and B

Burghart-Stoll, Heike,Brueckner, Reinhard

supporting information; experimental part, p. 3978 - 4017 (2012/10/18)

Comprehensive comparisons of 1H and 13C NMR chemical shift values in the furanone cores a, b, and c provide plausible support for a reassessment of the furanone nuclei of the title compounds from b to c. Total syntheses via enantiomerically pure lactic esters were based on the Seebach-Frater "self-reproduction of stereocenters" methodology. Attachment of the hexadienyl side-chain in a trans,trans-selective manner was achieved by addition of the Seebach-Frater enolate to trans-hex-4-en-1-al rather than to trans-hex-3-en-1-al. The type-c furanone cores of the synthetic materials were reached by single or double acylation of a model γ-hydroxy-β-oxo ester (compound 50) and its hexadiene-containing counterpart 29. Our syntheses confirmed the novel connectivities in six compounds. In addition, they required revision of the configuration of a quaternary carbon atom in five cases. Moreover, they allowed elucidation of the configurations of four previously unassigned stereocenters. Hindsight analyses of why the furanone cores of the title compounds had been misinterpreted as a and/or b instead of c are given. Why the stereocenters in the heterocycles had been incorrectly configured, on the bases (a) of relay studies in the 1960s, and (b) of a 1984 total synthesis of gregatin B, is also discussed.

Mycenaaurin A, an antibacterial polyene pigment from the fruiting bodies of mycena aurantiomarginata

Jaeger, Robert J. R.,Spiteller, Peter

experimental part, p. 1350 - 1354 (2010/10/21)

A new polyene pigment, mycenaaurin A (1), was isolated from fruiting bodies of Mycena aurantiomarginata. Mycenaaurin A consists of a tridecaketide that is flanked by two amino acid moieties. These are likely to be derived biosynthetically from S-adenosylmethionine. The tridecaketide itself contains an α-pyrone, a conjugated hexaene, and an isolated alkenyl moiety. The structure of the new pigment was established by 2D NMR spectroscopic methods and APCIMS. The absolute configuration of the four stereogenic centers was determined by degradation of 1 by ozonolysis and GC-MS comparison of the resulting fragments, after appropriate derivatization, with authentic synthetic samples. Mycenaaurin A (1) might act as a constitutive defense compound, since it exhibits antibacterial activity against the Gram-positive bacterium Bacillus pumilus.

Asymmetric hydrolysis of 2-hydroxy-carboxylic esters using recombinant Escherichia coli

Nakagawa, Atsushi,Kato, Ko,Shinmyo, Atsuhiko,Suzuki, Toshio

, p. 2394 - 2398 (2008/03/13)

Optically active 2-hydroxy-carboxylates are important compounds for their use as intermediates in the synthesis of pharmaceuticals and stereoblock polymers. Enterobacter sp. DS-S-75 and the recombinant Escherichia coli harbouring the 4-chloro-3-hydroxybutyrate (CHB) hydrolase gene from the strain DS-S-75 showed asymmetric hydrolytic activity towards 2-hydroxy-carboxylates, as well as towards CHB. It was discussed that the hydroxyl group in the substrate was particularly important for the asymmetric hydrolytic activity of the CHB hydrolase, and as such, it was re-designated to EnHCH (hydroxy-carboxylic ester hydrolase derived from Enterobacter sp.). Using the recombinant cell, both the reaction rate and the concentration of the substrates were significantly improved upon when compared to that of DS-S-75. Optically active 2-hydroxy-carboxylates could be synthesized on a practical basis for industrial production in this report.

KETOGENIC SACCHARIDES

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Page/Page column 8, (2008/06/13)

A novel ketogenic compound is provided having general formula (R(OCH(CH3)CH2C(O))nO)m-A wherein n is a integer between I and 10, m is an integer of 1 to 200,000, A is a monsaccharide, polysaccharide or oligosaccharide residue and R is selected from the group consisting of H, C1-C6 alkyl and acetoacetyl-

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