3-hydroxybutyric acid

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Structural formula
Structure of (±) -3-hydroxybutyric acid
Structural formula without information on stereochemistry
General
Surname 3-hydroxybutyric acid
other names
  • 3-hydroxybutanoic acid
  • β-hydroxybutyric acid
Molecular formula C 4 H 8 O 3
Brief description

colorless liquid with an unpleasant odor

External identifiers / databases
CAS number
  • 300-85-6 (unspecified mixture of enantiomers)
  • 625-72-9 [( R ) -3-hydroxybutyric acid]
  • 6168-83-8 [( S ) -3-hydroxybutyric acid]
  • 625-71-8 [(±) -3-hydroxybutyric acid]
EC number 206-099-9
ECHA InfoCard 100.005.546
PubChem 441
ChemSpider 428
Wikidata Q223092
properties
Molar mass 104.10 g mol −1
Physical state

liquid

density

1.16 g cm −3

boiling point

118–120 ° C (3 h Pa )

solubility
safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 280-332 + 313-337 + 313-261-302 + 352-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

3-Hydroxybutyric acid , systematically 3-hydroxybutanoic acid , is a chemical compound from the group of hydroxycarboxylic acids . Their salts are called 3-hydroxybutyrates.

Isomers

3-Hydroxybutyric acid occurs in two enantiomeric forms [( R ) -3-hydroxybutyric acid and ( S ) -3-hydroxybutyric acid].

Isomers of 3-hydroxybutyric acid
Surname ( R ) -3-hydroxybutyric acid ( S ) -3-hydroxybutyric acid
other names (-) - 3-Hydroxybutyric acid
D -3-hydroxybutyric acid		 (+) - 3-Hydroxybutyric acid
L -3-Hydroxybutyric acid
Structural formula 3-Hydroxybutyric acid Enantiomers Structural Formulase.svg
CAS number 625-72-9 6168-83-8
300-85-6 (unspec.)
EC number 210-909-6 228-209-4
206-099-9 (unspec.)
ECHA info card 100.009.918 100.025.646
100.005.546 (unspec.)
PubChem 92135 -
441 (unspec.)
Wikidata Q27075135 Q27075158
Q223092 (unspec.)

Occurrence

D -3-hydroxybutyric acid occurs naturally in the metabolism of animals. It is one of three so-called keto bodies . It is produced in the liver from acetoacetic acid with the help of the enzyme D- β-hydroxybutyrate dehydrogenase and is excreted in the urine , the proportion being increased there in ketosis (acetonuria).

presentation

From acetoacetic ester formed by reaction with sodium amalgam in the cold ( RS -3-hydroxybutyric acid).

Synthesis of 3-hydroxybutyric acid from acetoacetic ester

From 1-chloro-2-propanol is reacted with potassium cyanide in ethanol , the corresponding nitrile is formed, which by hydrolysis can be converted to 3-hydroxybutyric acid.

Synthesis of 3-hydroxybutyric acid from 1-chloro-3-butanol

Reactions

When 3-hydroxybutyric acid is heated, crotonic acid is formed with elimination of water :

Synthesis of crotonic acid from 3-hydroxybutanoic acid

use

3-Hydroxybutyric acid can be used industrially for the production of biodegradable plastics ( polyhydroxybutyric acid ).

The butyl ester 3-hydroxybutyric acid butyl ester is a solvent.

See also

Individual evidence

  1. ↑ a b c d e f Entry on 3-hydroxybutyric acid in the GESTIS substance database of the IFA , accessed on January 16, 2020(JavaScript required) .
  2. ↑ Material Safety Data Sheet 3-Hydroxybutyric Acid at coleparmer.com.
  3. ^ A b F. Beilstein: Handbook of organic chemistry , 3rd edition, 1st volume. Verlag Leopold Voss, 1893. P. 561. Full text
  4. ^ F. Beilstein: Handbook of organic chemistry , 3rd edition, 1st volume. Verlag Leopold Voss, 1893. S. 506. Full text
  5. ↑ Patent EP0355307 : Extraction agent for poly-D (-) - 3-hydroxybutyric acid. Registered on June 21, 1989 , published on December 28, 1994 , Applicant: PCD Polymers Society, Inventors: Heinz Traussnig, Engelbert Kloimstein, Hans Kroath, Robert Estermann. ‌