Description References
ChemicalBook > CAS DataBase List > L-Homophe-OH

L-Homophe-OH

Description References
Product Name
L-Homophe-OH
CAS No.
943-73-7
Chemical Name
L-Homophe-OH
Synonyms
HOMOPHENYLALANINE;(S)-2-AMINO-4-PHENYLBUTANOIC ACID;HPHE;LHPA;(S)-APBA;H-HPH-OH;H-HFE-OH;L-HPhe-OH;L-HOMOPHE;H-L-HPA-OH
CBNumber
CB8206268
Molecular Formula
C10H13NO2
Formula Weight
179.22
MOL File
943-73-7.mol
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L-Homophe-OH Property

Melting point:
>300 °C(lit.)
alpha 
45 º (C=1, 3N HCl 19 ºC)
Boiling point:
311.75°C (rough estimate)
Density 
1.1248 (rough estimate)
refractive index 
44 ° (C=1, 3mol/L HCl)
storage temp. 
Keep in dark place,Inert atmosphere,Room temperature
solubility 
Soluble in dilute aqueous acid.
pka
2.32±0.10(Predicted)
form 
Solid
color 
White to Off-White
InChI
InChI=1/C10H13NO2/c11-9(10(12)13)7-6-8-4-2-1-3-5-8/h1-5,9H,6-7,11H2,(H,12,13)/t9-/s3
InChIKey
JTTHKOPSMAVJFE-VIFPVBQESA-N
SMILES
C(O)(=O)[C@H](CCC1=CC=CC=C1)N |&1:3,r|
CAS DataBase Reference
943-73-7(CAS DataBase Reference)
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Safety

Hazard Codes 
Xi
Safety Statements 
22-24/25
WGK Germany 
3
HS Code 
29224999
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TCI Chemical
Product number
H0985
Product name
L-Homophenylalanine
Purity
>98.0%(T)
Packaging
1g
Price
$52
Updated
2024/03/01
TCI Chemical
Product number
H0985
Product name
L-Homophenylalanine
Purity
>98.0%(T)
Packaging
100mg
Price
$16
Updated
2024/03/01
Alfa Aesar
Product number
H27295
Product name
L-Homophenylalanine, 98%
Packaging
1g
Price
$61.65
Updated
2024/03/01
Alfa Aesar
Product number
H27295
Product name
L-Homophenylalanine, 98%
Packaging
5g
Price
$179.65
Updated
2024/03/01
Alfa Aesar
Product number
H27295
Product name
L-Homophenylalanine, 98%
Packaging
25g
Price
$559.65
Updated
2024/03/01
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L-Homophe-OH Chemical Properties,Usage,Production

Description

L-Homophenylalanine is an amino acid derivative. It has been extensively used in the pharmaceutical industry as a precursor for production of angiotensin-converting enzyme (ACE) inhibitor: enalapril, delapril, quinapril and ramipril, which possesses significant clinical application in the management of hypertension and congestive heart failure (CHF). It acts as an anti-tumor reagent.

References

Hwang, J. Y., et al. "Simultaneous synthesis of 2-phenylethanol and L-homophenylalanine using aromatic transaminase with yeast Ehrlich pathway." Biotechnology & Bioengineering 102.5(2009):1323-9.
Ahmad, A. L., P. C. Oh, and S. R. Abd Shukor. "Sustainable biocatalytic synthesis of L-homophenylalanine as pharmaceutical drug precursor."Biotechnology Advances 27.3(2009):286-296.
https://www.alfa.com/en/catalog/H27295/

Application

L-homophenylalanine is used almost exclusively as single stereoisomer in pharmaceutical drug production. L-homophenylalanine as a common building block, due to the presence of L-homophenylalanine moiety as the central pharmacophore unit. L-homophenylalanine is also an important chiral intermediate to synthesize a variety of novel pharmaceuticals including β-lactam antibiotics, acetylcholinesterase inhibitor and neutral endopeptidace (NEP) inhibitor which retained their status as major contributors to human health preservation. L-homophenylalanine acts as a precursor for the synthesis of NEP inhibitors, which complements the effects of ACE inhibitors when used simultaneously, potentiates the outcome in the management of hypertension and congestive heart failure[1].

Chemical Properties

White Solid

Uses

L-Homophenylalanine is used as a precursor in the pharmaceutical industry for the production of angiotensin-converting enzyme (ACE) and R-(-)-Homophenylalanin-ethylester. It is also involved in the synthesis of NEPA [(S,S)-N-(1-Ethoxycarbonyl-3-phenylpropyl)alanine], which is a key intermediate to prepare the ACE-inhibitors: enalapril, delapril, quinapril and ramipril. It acts as an anti-tumor reagent.

Uses

Antitumor agent.

Definition

ChEBI: A non-proteinogenic L-alpha-amino acid that is an analogue of L-phenylalanine having a 2-phenylethyl rather than a benzyl side-chain.

Production Methods

Asymmetric reduction of prochiral ketone remains one of the most investigated methods to date for production of chiral L-homophenylalanine. One of the most established method for synthesizing L-homophenylalanine on a laboratory scale was carried out via enzyme-catalyzed asymmetric synthesis of keto acids. In this method, prochiral ketone was converted via reductive amination to enantiopure products with bulky side chains by addition of biocatalysts such as L-homophenylalanine dehydrogena. in the presence of cofactor. L-phenylalanine dehydrogenase is by and large preferred as it has mainly a catabolic function and accepts a wide variety of keto acids as substrates hence it is generally employed in the synthesis of L-homophenylalanine which carries very bulky side chains[1].

References

[1] Ahmad A, et al. Sustainable biocatalytic synthesis of L-homophenylalanine as pharmaceutical drug precursor. Biotechnology Advances, 2009; 27: 286-296.

L-Homophe-OH Preparation Products And Raw materials

Raw materials

Preparation Products

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L-Homophe-OH Suppliers

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View Lastest Price from L-Homophe-OH manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
L-Homophenylalanine 943-73-7
Price
US $0.00/Kg/Drum
Min. Order
1KG
Purity
98.0%-101.0%
Supply Ability
500kg
Release date
2021-07-28
Sichuan HongRi Pharma-Tech Co.,Ltd
Product
L-Homophe-OH 943-73-7
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1T+
Release date
2023-09-25
Hebei Weibang Biotechnology Co., Ltd
Product
L-Homophenylalanine 943-73-7
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
500000kg
Release date
2024-11-04

943-73-7, L-Homophe-OHRelated Search:

4-(4-Aminophenyl)butyric acid Boc-D-Tyr-OH ALTRENOGEST α-Lipoic Acid L(+)-Arginine Glycine Betaine 4-Phenylbutyric acid METHYL 4-(4-AMINOPHENYL)BUTANOATE 4-Aminobutyric acid L-Homophenylalanine ethyl ester hydrochloride Phenylacetone N-[(tert-Butoxy)carbonyl]-D-tryptophan FMOC-4-TRIFLUOROMETHYL-D-BETA-HOMOPHENYLALANINE BOC-(S)-3-AMINO-4-(4-CHLORO-PHENYL)-BUTYRIC ACID [-/+]-2-AMINO-4-PHENYLBUTYRIC ACID,DL-ALPHA-AMINO-4-PHENYLBUTYRIC ACID 2,4-DICHLORO-L-BETA-HOMOPHENYLALANINE HYDROCHLORIDE N-T-BUTOXYCARBONYL-(S)-3-AMINO-4-PHENYLBUTYRIC ACID,(S)-3-(BOC-AMINO)-4-PHENYLBUTYRIC ACID

  • (+)-2-Amino-4-phenylbutyric acid,98%
  • S)-α-Amino-benzenebutanoic acid
  • L-(S)-Homophenylalanine.HCl
  • L-Homophenylalanine ,98%
  • H-L-HPA-OH
  • Benzenebutanoicacid, a-aMino-, (aS)-
  • H-HoMophe-OH(HoMophenylalanine)
  • RARECHEM BK PT 0049
  • (S)-2-AMINO-4-PHENYLBUTANOIC ACID
  • (S)-(+)-2-AMINO-4-PHENYLBUTYRIC ACID
  • (S)-2-AMINO-4-PHENYLBUTYRIC ACID
  • (S)-HOMOPHENYLALANINE
  • (2S)-2-Amino-4-phenylbutyric acid
  • (S)-APBA
  • Benzenebutanoic acid, α-amino-, (αS)-
  • (aS)-α-Aminobenzenebutanoic Acid
  • L-Benzylalanine
  • L--Phenylbutyrine
  • (aS)-a-Aminobenzenebutanoic Acid
  • L-HOMOPHENYLALANINE extrapure
  • L-HPhe-OH
  • Benzenebutanoic acid, alpha-amino-, (S)-
  • Fmoc-4-nitro-L-&beta
  • Boc-D-&beta
  • Benzenebutanoic acid, .alpha.-amino-, (.alpha.S)-
  • L-Homophe-OH
  • (αS)-α-Amino-benzenebutanoic Acid,99%e.e.
  • 2-(S)-AMINO-4-PHENYLBUTANOIC ACID
  • L-ALPHA-AMINO-4-PHENYLBUTYRIC ACID
  • L-2-AMINO-4-PHENYLBUTYRIC ACID
  • L-HOMOPHE
  • L-(+)-HOMOPHENYLALANINE
  • L-HOMOPHENYLALANINE
  • LHPA
  • HPHE
  • H-HPH-OH
  • H-HOMOPHE-OH
  • H-HOPHE-OH
  • H-HFE-OH
  • HOMO-L-PHENYLALANINE
  • HOMOPHENYLALANINE, L-
  • HOMOPHENYLALANINE
  • L- Homophenylalanine (LHPA)
  • Homophenyl-L-alanine
  • (+)-2-Amino-4-phenylbutyric acid
  • H-L-HPhe-OH
  • L-Homophenylalanine, (S)-2-Amino-4-phenyl-butyric acid
  • L-Homophenylalanine99%
  • L-Homophenylalanine 99%
  • (2R)-2-amino-4-phenylbutanoic acid
  • (S)-ALPHA-AMINOBENZENEBUTANOIC ACID
  • (2S)-2-ammonio-4-cyclohexylbutanoate
  • L-Homophenylalanine&gt
  • -HomophenyL
  • L-Homophenylalanine USP/EP/BP
  • TIANFUCHEM--943-73-7---L-Homophenylalanine
  • L-Homophenylalanine,97%
  • (αS)?-α-?Amino-benzenebutanoic Acid