Phenylacetyl carbinol

Structural formula
General
Surname	Phenylacetyl carbinol
other names	1-Hydroxy-1-phenyl-propan-2-one PAC
Molecular formula	C 9 H 10 O 2
External identifiers / databases
CAS number 90-63-1 EC number 202-006-0 ECHA InfoCard 100.001.824 PubChem 92733 Wikidata Q413710
properties
Molar mass	150.17 g mol −1
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 302-312-315-319-332-335 P: ?
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Phenylacetylcarbinol (PAC) is a ketone with one phenyl group and one hydroxy group .

A catalytic reduction in the presence of methylamine converts phenylacetylcarbinol - via the intermediate stage of the imine - to ephedrine .

synthesis

Phenylacetylcarbinol is produced microbiologically from the starting materials benzaldehyde and acetaldehyde .

${\displaystyle \mathrm {C_{6}H_{5}CHO+CH_{3}CHO\longrightarrow C_{6}H_{5}CHOHCOCH_{3}} }$

PAC can also consider the factors thiamine and magnesium - ions from the reaction of pyruvic acid and benzaldehyde win. Carbon dioxide is produced as a by-product .

${\displaystyle \mathrm {CH_{3}COCOOH+\ C_{6}H_{5}CHO\longrightarrow } }$

${\displaystyle \mathrm {C_{6}H_{5}CHOHCOCH_{3}+\ CO_{2}} }$

Stereoisomers

Phenylacetyl carbinol
Surname	(R) -phenylacetylcarbinol	(S) -Phenylacetylcarbinol
Other name	L - (-) - phenylacetylcarbinol (1 R ) -1-Hydroxy-1-phenyl-propan-2-one	D - (-) - Phenylacetylcarbinol (1 S ) -1-Hydroxy-1-phenyl-propan-2-one
Structural formula
CAS number	1798-60-3	53439-91-1
PubChem	9920426	9815225
ECHA info card	100,015,715
EC number	217-285-4

literature

• PF Smith, D. Hendlin: Further studies on phenylacetylcarbinol synthesis by yeast. In: Applied Microbiology . Volume 2, Number 5, September 1954, pp. 294-296, PMID 13208181 , PMC 1057016 (free full text).
• Purer PAC production from yeast (English; PDF file; 1.17 MB)

Individual evidence

1. ↑ There is not yet a harmonized classification for this substance . A labeling of 1-hydroxy-1-phenylacetone in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on July 10, 2020, is reproduced from a self-classification by the distributor .