L-Homophenylalanine

Iupac Name：(2S)-2-amino-4-phenylbutanoic acid

Molecular Weight：179.219

Modify Date.: 2022-11-29 06:00

Introduction: 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. View more+

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1. Names and Identifiers

1.1 Name: L-Homophenylalanine
1.2 Synonyms: (+)-(S)-Homophenylalanine (+)-Homophenylalanine (+)-L-Homophenylalanine (2S)-2-Amino-4-phenylbutanoic acid (2S)-2-Azaniumyl-4-phenylbutanoate (S)-2-Amino-4-phenylbutyric Acid (S)-Homophenylalanine (αS)-α-Aminobenzenebutanoic acid Benzenebutanoic acid, α-amino-, (S)- Benzenebutanoic acid, α-amino-, (αS)- Butyric acid, 2-amino-4-phenyl-, L- H-Homophe-OH H-HoMophe-OH(HoMophenylalanine) H-L-HPA-OH L-(S)-Homophenylalanine.HCl L-2-Amino-4-phenylbutyric acid L-Benzylalanine L-γ-Phenylbutyrine RARECHEM BK PT 0049

1.3 CAS No.: 943-73-7

1.4 CID: 2724505

1.5 EINECS(EC#): 213-403-3

1.6 Molecular Formula: C10H13NO2 (isomer)

1.7 Inchi: InChI=1S/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-/m0/s1

1.8 InChkey: JTTHKOPSMAVJFE-VIFPVBQESA-N

1.9 Canonical Smiles: C1=CC=C(C=C1)CCC(C(=O)O)N

1.10 Isomers Smiles: C1=CC=C(C=C1)CC[C@@H](C(=O)O)N

2. Properties

2.1 Density: 1.164

2.1 Melting point: 300℃

2.1 Boiling point: 324.8°Cat760mmHg

2.1 Refractive index: 44 ° (C=1, 3mol/L HCl)

2.1 Flash Point: 150.2°C

2.1 Precise Quality: 179.09500

2.1 PSA: 63.32000

2.1 logP: 1.73140

2.1 Solubility: Soluble in dilute aqueous acid.

2.2 Appearance: Off-White crystalline powder

2.3 Storage: Ambient temperatures.

2.4 Chemical Properties: White Solid

2.5 pKa: 2.32±0.10(Predicted)

2.6 Water Solubility: soluble in dilute aqueous acid.

2.7 Stability: Stable under normal temperatures and pressures.

2.8 StorageTemp: Store at RT.

3. Use and Manufacturing

3.1 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. L-HomophenylalanineSupplier

3.2 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 1 of 2 companies. For more detailed information, please visit ECHA C&L website

Of the 1 notification(s) provided by 1 of 2 companies with hazard statement code(s):

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501

3.3 Usage: Antitumor agent.

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Safety Statements: S24/25

4.1 Hazard Declaration: H315

4.1 Caution Statement: P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

4.1 WGK Germany: 3

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

View all

6. Synthesis Route

943-73-7Total: 48 Synthesis Route

710-11-2 64 Suppliers

943-73-7 229 Suppliers

Literatures:
Asano; Yamada; Kato; Yamaguchi; Hibino; Hirai; Kondo Journal of Organic Chemistry, 1990 , vol. 55, # 21 p. 5567 - 5571
Yield: ~96%

103-63-9 294 Suppliers

943-73-7 229 Suppliers

Literatures:
Journal of Organic Chemistry, , vol. 55, # 21 p. 5567 - 5571
Yield: null

104-53-0 71 Suppliers

943-73-7 229 Suppliers

Literatures:
Advanced Synthesis and Catalysis, , vol. 354, # 17 p. 3327 - 3332
Yield: null

View all

7. Precursor and Product

precursor:

16503-46-1

6783-05-7

99169-43-4

46460-23-5

104-53-0

253327-94-5

212832-72-9

108960-95-8

1012-05-1

17812-07-6

5440-40-4

591-50-4

422511-01-1

710-11-2

96613-91-1

64920-29-2

530-36-9

103-63-9

92397-73-4

139040-47-4

23190-16-1

92397-74-5

View all

product :

82717-96-2

64920-29-2

89396-94-1

89371-44-8

90891-21-7

8. Other Information

8.0 Usage: 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.

8.1 Mesh Entry Terms: (S)-2-amino-4-phenylbutanoic acid

9. Computational chemical data

Molecular Weight: 179.219g/mol
Molecular Formula: C₁₀H₁₃NO₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 179.094628657
Monoisotopic Mass: 179.094628657
Complexity: 164
Rotatable Bond Count: 4
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 3
Topological Polar Surface Area: 63.3
Heavy Atom Count: 13
Defined Atom Stereocenter Count: 1
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccByMAAAAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAHgAQCAAADCjBmAQwCIBAAgCIAiDSCAACAAAgAAAIiIGAAIgKIDKAkRCAYAAkkAAIiAeYyLCOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==