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943-73-7

Basic Information
CAS No.: 943-73-7
Name: Benzenebutanoicacid, a-amino-, (aS)-
Molecular Structure:
Molecular Structure of 943-73-7 (Benzenebutanoicacid, a-amino-, (aS)-)
Formula: C10H13NO2
Molecular Weight: 179.22 .
Synonyms: L-g-Phenylbutyrine;L-Home-phenylalanine;(S)-2-Amino-4-Phenylbutanoic Acid;H-HomoPhe-OH;Benzenebutanoicacid, a-amino-, (S)-;Butyric acid,2-amino-4-phenyl-, L- (8CI);(+)-Homophenylalanine;(2S)-2-Amino-4-phenylbutanoic acid;L-2-Amino-4-phenylbutyric acid;
EINECS: 213-403-3
Density: 1.164 g/cm3
Melting Point: >300 °C(lit.)
Boiling Point: 324.8 °C at 760 mmHg
Flash Point: 150.2 °C
Solubility:
Appearance: white solid
Hazard Symbols: IrritantXi
Risk Codes:  Xi:;
">  Xi:;
Safety: 22-24/25
Transport Information:
PSA: 63.32000
LogP: 1.73140
Synthetic route

S-2-amino-4-carbonyl-4-phenylbutyric acid hydrochloride

943-73-7

D-homophenylalanine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In hydrogenchloride at 55℃; under 760 Torr;100%
With hydrogenchloride; palladium 10% on activated carbon; hydrogen In water at 90℃; under 1500.15 Torr;92%
With hydrogen; acetic acid; palladium on activated charcoal In water at 20℃; for 6h;
1239710-15-6

methyl (2S)-4-phenyl-2-(trichloromethylcarbonylamino)butanoate

943-73-7

D-homophenylalanine

Conditions
ConditionsYield
With hydrogenchloride; water for 20h; Inert atmosphere; Reflux;100%
710-11-2

2-oxo-4-phenylbutyric acid

943-73-7

D-homophenylalanine

Conditions
ConditionsYield
With formate dehydrogenase; NAD; ammonium formate at 30℃; for 24h; PheDH;99%
With formate dehydrogenase; ammonium formate; β-nicotinamide adenine dinucleotide reduced In aq. buffer at 30℃; for 24h; pH=8.5; Enzymatic reaction;80%
With L-phenylalanine; phenylalanine dehydrogenase; pyridoxal 5'-phosphate; alcohol dehydrogenases from Bacillus stearothermophilus; aromatic aminotransferase; NADH In isopropyl alcohol at 35℃; for 2h; pH=8; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;60.3%
With glucose dehydrogenase; ammonium sulfate; D-glucose; NADP+-specific glutamate dehydrogenase from Pseudomonas putida, K402F mutant; nicotinamide adenine dinucleotide phosphate In aq. buffer at 35℃; pH=7.5; Reagent/catalyst; Green chemistry; Enzymatic reaction; enantioselective reaction;n/a
422511-01-1

(RS)-homophenylalaninamide hydrochloride

943-73-7

D-homophenylalanine

Conditions
ConditionsYield
With pyridoxal 5'-phosphate monohydrate; cobalt(II) chloride In aq. buffer at 40℃; for 12h; pH=7.0; Enzymatic reaction;99%

L-(+)-homophenylalanine hydrochloride

943-73-7

D-homophenylalanine

Conditions
ConditionsYield
With sodium carbonate In methanol for 0.0833333h;98%
139040-47-4

(S)-2-Azido-4-phenyl-butyric acid

943-73-7

D-homophenylalanine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethyl acetate under 760 Torr; for 13h;92%
With hydrogen; palladium on activated charcoal In methanol
100516-57-2

(3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(2'-oxo-2'-phenylethyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

A

943-73-7

D-homophenylalanine

B

82795-51-5

D-homophenylalanine

Conditions
ConditionsYield
With hydrogen; palladium dichloride In tetrahydrofuran; ethanol under 2068.6 Torr; for 34h; Yields of byproduct given;A 91%
B n/a

C10H12N2O4

943-73-7

D-homophenylalanine

Conditions
ConditionsYield
With 10 wt% Pd(OH)2 on carbon; hydrogen In ethanol; water at 65℃;91%
108960-95-8

homophenylalanine sodium salt

943-73-7

D-homophenylalanine

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide In water89.6%

C18H21NO3

943-73-7

D-homophenylalanine

Conditions
ConditionsYield
With 20% palladium hydroxide-activated charcoal; hydrogen In methanol at 45℃; under 760.051 Torr; for 7h; Reagent/catalyst; Inert atmosphere; Green chemistry;85%
5440-40-4

2-(acetylamino)-4-phenylbutanoic acid

A

943-73-7

D-homophenylalanine

B

5440-40-4, 60505-02-4, 96613-91-1, 63393-59-9

(2R)-N-acetyl-2-amino-4-phenylbutyric acid

Conditions
ConditionsYield
With L-aminoacylase; cobalt(II) chloride In aq. buffer at 20 - 38℃; for 1h; pH=7.5; Inert atmosphere; Resolution of racemate; Enzymatic reaction; enantioselective reaction;A 39%
B 51%
With sodium hydroxide; potassium phosphate buffer; beef kidney acetone; CoCl2 at 37℃; for 24h; pH=7.5; Enzymatic reaction;A 41%
B 37.5%
With aminoacylase from Aspergillus oryzae; cobalt(II) chloride In water at 37℃; for 34h;A 38%
B 37%
With cobalt(II) chloride at 30℃; pH=8; aq. phosphate buffer; Resolution of racemate; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;

(3aS,7S)-2,7-Diphenyl-tetrahydro-isoxazolo[3,2-c][1,4]oxazin-4-one

943-73-7

D-homophenylalanine

Conditions
ConditionsYield
With hydrogen; palladium dihydroxide In 1,4-dioxane; trifluoroacetic acid under 3102.89 Torr;50%
1821-12-1

4-Phenylbutyric acid

943-73-7

D-homophenylalanine

Conditions
ConditionsYield
Stage #1: 4-Phenylbutyric acid With P450CLA; dihydrogen peroxide In aq. phosphate buffer; ethanol at 20℃; for 20h; pH=7; Enzymatic reaction;
Stage #2: With D-HIC-DH; L-HIC-DH; L-Phe-DH; NAD; ammonium carbonate; ammonium chloride In aq. phosphate buffer; ethanol at 20℃; for 24h; pH=8; Enzymatic reaction; enantioselective reaction;
48%
Stage #1: 4-Phenylbutyric acid With P450CLA; dihydrogen peroxide In aq. phosphate buffer; ethanol at 20℃; for 24h; pH=7; Enzymatic reaction;
Stage #2: With D-isocaproate dehydrogenase from Lactobacillus confuses; L-isocaproate dehydrogenase from Lactobacillus confuses; L-phenylalanine dehydrogenase from Rhodococcus sp.; NAD; ammonium carbonate; ammonium chloride In aq. phosphate buffer; ethanol for 24h; pH=8; Enzymatic reaction; enantioselective reaction;
48%
96613-91-1

(R)-2-Acetamido-4-phenylbutansaeure

943-73-7

D-homophenylalanine

Conditions
ConditionsYield
With hydrogenchloride
With phosphoric acid
13735-81-4

1-styrenyloxytrimethylsilane

100570-94-3

(5S,6R)-3-Bromo-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

943-73-7

D-homophenylalanine

Conditions
ConditionsYield
With hydrogen; zinc(II) chloride; palladium dichloride 1.) THF, 25 deg C, 2.) EtOH, 25 deg C, p= 20 psi; Yield given. Multistep reaction;
5440-40-4

2-(acetylamino)-4-phenylbutanoic acid

943-73-7

D-homophenylalanine

Conditions
ConditionsYield
With CoCl2 In water at 37℃; for 72h; aminoacylase (from Aspergillus oryzae); pH 7;
With aminoacylase I from Aspergillus melleus; Tris buffer In water at 25℃; pH=7.5;
100-44-7

benzyl chloride

[(S)-2-N-(N-benzylprolyl)aminobenzophenone-Δ-Ala]Ni(II)

A

943-73-7

D-homophenylalanine

B

82795-51-5

D-homophenylalanine

Conditions
ConditionsYield
With hydrogenchloride; 2,2'-azobis(isobutyronitrile); water; tri-n-butyl-tin hydride Product distribution; various alkyl halides, stereoselective addition;
212832-72-9

-2-<(benzyloxycarbonyl)amino>-4-phenyl-3-butenoic acid

943-73-7

D-homophenylalanine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol for 4h; Ambient temperature;
201852-41-7

[(E)-(S)-1-((S)-1,2-Dihydroxy-ethyl)-3-phenyl-allyl]-carbamic acid tert-butyl ester

943-73-7

D-homophenylalanine

Conditions
ConditionsYield
With ruthenium trichloride; sodium periodate In tetrachloromethane; water; acetonitrile

benzyl 2-amino-4-phenylbutanoate

A

943-73-7

D-homophenylalanine

B

82795-51-5

D-homophenylalanine

Conditions
ConditionsYield
With Alcalase; water In tert-butyl alcohol at 25℃; for 0.3h; pH=8.5; kinetic resolution; Title compound not separated from byproducts;
(+-)-2-amino-4-phenyl-butyric acid amide

(+-)-2-amino-4-phenyl-butyric acid amide

943-73-7

D-homophenylalanine

Conditions
ConditionsYield
With aminopeptidase-substance from pig's-kidneys; water; manganese(ll) chloride at 38℃; pH 7.5;
253327-94-5

(S)-2-acetamido-4-phenylbutyric acid ethyl ester

943-73-7

D-homophenylalanine

Conditions
ConditionsYield
With hydrogenchloride for 2h; Hydrolysis; Heating;

(S)-3-((S)-2-Hydroxy-1-phenyl-ethylamino)-5-phenyl-dihydro-furan-2-one

943-73-7

D-homophenylalanine

Conditions
ConditionsYield
With hydrogen; palladium dihydroxide In 1,4-dioxane; trifluoroacetic acid under 3102.89 Torr;
99169-43-4, 124019-00-7, 85808-34-0

DL-2-amino-4-phenylbutyramide

A

943-73-7

D-homophenylalanine

B

82795-51-5

D-homophenylalanine

Conditions
ConditionsYield
With aminoacylase I from Aspergillus melleus; Tris buffer In water at 25℃; for 2.5h; pH=7.5; Title compound not separated from byproducts;
Multi-step reaction with 2 steps
1: hydrogenchloride / water / 3 h / 20 °C
2: pyridoxal 5'-phosphate monohydrate / aq. buffer / 12 h / 40 °C / pH 8.0 / Enzymatic reaction
View Scheme

(3E,2S)-2-amino-4-phenyl-3-butenoic acid hydrochloride

943-73-7

D-homophenylalanine

Conditions
ConditionsYield
With hydrogen; acetic acid; palladium on activated charcoal In water at 20℃; for 6h;

(4R,5S)-1,5-Dimethyl-4-phenyl-3-(4-phenyl-butyryl)-imidazolidin-2-one

943-73-7

D-homophenylalanine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: LHMDS / tetrahydrofuran; hexane / -78 °C
1.2: Br2 / tetrahydrofuran; hexane / -78 °C
2.1: 92 percent / tetramethylguanidinium azide / CH2Cl2 / 0 - 20 °C
3.1: 95 percent / LiOH; aq. H2O2 / tetrahydrofuran / 20 °C
4.1: H2 / Pd/C / methanol
View Scheme
852298-76-1

(2'R,4S,5R)-1-(2'-bromo-4'-phenylbutyryl)-3,4-dimethyl-5-phenylimidazolidin-2-one

943-73-7

D-homophenylalanine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 92 percent / tetramethylguanidinium azide / CH2Cl2 / 0 - 20 °C
2: 95 percent / LiOH; aq. H2O2 / tetrahydrofuran / 20 °C
3: H2 / Pd/C / methanol
View Scheme
852298-83-0

(4S,5R)-1-((S)-2-Azido-4-phenyl-butyryl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one

943-73-7

D-homophenylalanine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / LiOH; aq. H2O2 / tetrahydrofuran / 20 °C
2: H2 / Pd/C / methanol
View Scheme
1012-05-1

D,L-homophenylalanine

943-73-7

D-homophenylalanine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: alkaline aq. solution / 0.5 h / 4 °C / pH 11
2: aminoacylase I from Aspergillus melleus; Tris buffer / H2O / 25 °C / pH 7.5
View Scheme
Multi-step reaction with 2 steps
1: 89.5 percent / NaOH / H2O / 1 h / 0 - 5 °C / pH 11 - 11.5
2: 41 percent / potassium phosphate buffer; aq. NaOH; beef kidney acetone powder / CoCl2 / 24 h / 37 °C / pH 7.5 / Enzymatic reaction
View Scheme
Multi-step reaction with 2 steps
2: CoCl2 / H2O / 72 h / 37 °C / aminoacylase (from Aspergillus oryzae); pH 7
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydroxide / water / Cooling with ice
1.2: pH 2
2.1: penicillin G acylase from Achromobacter sp. CCM 4824; water / 30 °C / pH 7 / Enzymatic reaction
View Scheme
64-17-5

ethanol

943-73-7

D-homophenylalanine

90891-21-7

L-(+)-α-amino-4-phenylbutyric acid ethyl ester hydrochloride

Conditions
ConditionsYield
With hydrogenchloride for 2h; Heating;100%
With thionyl chloride at 60℃; for 5h;92%
With thionyl chloride
943-73-7

D-homophenylalanine

79-22-1

methyl chloroformate

136220-97-8, 148554-82-9, 96854-30-7

(S)-2-<(Methoxycarbonyl)amino>-4-phenylbutanoic Acid

Conditions
ConditionsYield
With sodium carbonate In water a) 0 deg C, 10 min, b) r.t., 2 h;100%
In tetrahydrofuran; water; sodium carbonate97%
With sodium carbonate In tetrahydrofuran at 20℃; for 4h;97%
67-56-1

methanol

943-73-7

D-homophenylalanine

60425-49-2

(+)-α-amino-4-phenylbutyric acid methyl ester hydrochloride

Conditions
ConditionsYield
With hydrogenchloride for 5h; Heating / reflux;100%
With thionyl chloride at 0 - 65℃; for 2h;95%
With thionyl chloride at 0 - 65℃; for 2h;95%
With thionyl chloride at 0 - 20℃;
943-73-7

D-homophenylalanine

27038-09-1

(2S)-2-amino-4-phenyl-1-butanol

Conditions
ConditionsYield
With lithium borohydride; Methyltrichlorosilane In tetrahydrofuran at 0℃; for 18.5h;97%
With lithium borohydride; chloro-trimethyl-silane In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;75%
Stage #1: D-homophenylalanine With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 18h; Reflux;
Stage #2: With water; sodium hydroxide In tetrahydrofuran
943-73-7

D-homophenylalanine

(S)-2-amino-4-cyclohexylbutanoic acid

Conditions
ConditionsYield
With hydrogenchloride; 5% rhodium-on-charcoal; platinum on carbon In methanol; water at 20℃; under 3102.97 Torr;97%
With hydrogenchloride; sodium hydroxide In water
With hydrogenchloride; 5% platinum on carbon; 5% Rh/C; hydrogen In methanol; water under 3102.97 Torr;
943-73-7

D-homophenylalanine

123-41-1

cholin hydroxide

choline-homophenylalanine

Conditions
ConditionsYield
In water at 3℃; Darkness;96%
943-73-7

D-homophenylalanine

174692-89-8

(S)-2-bromo-4-phenylbutanoic acid

Conditions
ConditionsYield
With hydrogen bromide; sodium nitrite In water at -10℃; for 3h;94%
3496-11-5

2,5-dioxopyrrolidin-1-yl (2S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanoate

943-73-7

D-homophenylalanine

N-benzyloxycarbonyl-L-valyl-L-homophenylalanine

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; water at 20℃; Condensation;89%
943-73-7

D-homophenylalanine

bis[2,2'-disulfan-diyl-4,4'-diphenyl]-dibutanoic acid

Conditions
ConditionsYield
Stage #1: D-homophenylalanine With hydrogen bromide; sodium nitrite In water for 0.666667h;
Stage #2: With sodium hydride; potassium thioacetate In N,N-dimethyl-formamide at 20℃; for 4h;
Stage #3: With sodium hydroxide In methanol at 20℃; for 3h;
89%
64-17-5

ethanol

943-73-7

D-homophenylalanine

46460-23-5

ethyl 2-amino-4-phenyl-(2S)-butyrate

Conditions
ConditionsYield
With hydrogenchloride; sodium carbonate84.9%
943-73-7

D-homophenylalanine

141-78-6

ethyl acetate

64920-29-2

2-oxo-4-phenylbutanoic acid ethyl ester

Conditions
ConditionsYield
With hydrogenchloride; sodium hypochlorite; tetrabutylammomium bromide In water at 0 - 40℃; Product distribution / selectivity;84.1%
943-73-7

D-homophenylalanine

107202-31-3

(S)-2-amino-4-cyclohexylbutyric acid hydrochloride

Conditions
ConditionsYield
With hydrogen; platinum In hydrogenchloride under 2585.7 Torr; for 16h;84%
943-73-7

D-homophenylalanine

100-51-6

benzyl alcohol

83080-02-8

benzyl (2S)-2-amino-4-phenylbutyrate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 16h; Dean-Stark; Reflux;80%
943-73-7

D-homophenylalanine

104-15-4

toluene-4-sulfonic acid

100-51-6

benzyl alcohol

117560-24-4

p-tolylsulfonic caid salt of L-homophenylalanine benzyl ester

Conditions
ConditionsYield
In toluene for 4h; Heating;79%
In benzene for 6h; Heating;
943-73-7

D-homophenylalanine

105226-92-4

(S,S)-2,4-dibenzylglutaric anhydride

112893-84-2

N-<(S,S)-2,4-dibenzyl-4-carboxybutyryl>-(S)-homophenylalanine

Conditions
ConditionsYield
With pyridine In dichloromethane for 16h; Ambient temperature;74%
943-73-7

D-homophenylalanine

3-bromo-2,3,4,5-tetrahydro-1H-[1]-benzoazepine-2-one-1-acetic acid tert-butyl ester

C26H32N2O5

Conditions
ConditionsYield
With triethylamine In isopropyl alcohol at 60℃; for 24h; Catalytic behavior; Concentration; Solvent; Temperature;73%
85-44-9

phthalic anhydride

943-73-7

D-homophenylalanine

291303-23-6

(S)-2-(1,3-dioxoisoindolin-2-yl)-4-phenylbutanoic acid

Conditions
ConditionsYield
With triethylamine In toluene at 130℃; Dean-Stark;72%
943-73-7

D-homophenylalanine

705919-70-6

L-4-nitro-homophenylalanine

Conditions
ConditionsYield
With sulfuric acid; nitric acid at 0 - 5℃; for 0.5h;59%
943-73-7

D-homophenylalanine

98-88-4

benzoyl chloride

150446-13-2

(S)-2-benzoylamino-4-phenylbutyric acid

Conditions
ConditionsYield
With sodium hydroxide In water at 0 - 23℃;59%
With sodium hydroxide cooling;
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    (2S)-2-ammonio-4-cyclohexylbutanoate

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    L-Homophenylalanine

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  • L-Homophenylalanine CAS: 943-73-7

  • Casno:

    943-73-7

    MSDS/COA Download

    L-Homophenylalanine CAS: 943-73-7

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    Formula:C10H13NO2 Molecular Weight:179.22 Synonyms:L-g-Phenylbutyrine;L-Home-phenylalanine;(S)-2-Amino-4-Phenylbutanoic Acid;H-HomoPhe-OH;Benzenebutanoicacid, a-amino-, (S)-;Butyric acid,2-amino-4-phenyl-, L- (8CI);(+)-Homophenylalanine;(2S)-2

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    943-73-7

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    943-73-7

    MSDS/COA Download

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    943-73-7

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    943-73-7

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  • L-Homophenylalanine CAS 943-73-7

  • Casno:

    943-73-7

    MSDS/COA Download

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  • Casno:

    943-73-7

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    943-73-7

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  • Casno:

    943-73-7

    L-Homophenylalanine

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    943-73-7

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  • Casno:

    943-73-7

    L-HOMOPHENYLALANINE

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  • Casno:

    943-73-7

    (S)-2-Amino-4-phenylbutyricacid

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    943-73-7

    L-Homophenylalanine

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    943-73-7

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    943-73-7

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    943-73-7

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  • Casno:

    943-73-7

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    943-73-7

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    943-73-7

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    943-73-7

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    943-73-7

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    943-73-7

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  • Casno:

    943-73-7

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Standards and Recommendations

APPEARANCE: Off-White crystalline powder
ASSAY (HPLC): 99.0% min
OPTICAL PURITY: 99.0% min
OPTICAL ROTATION: +45.5° ± 1°
LOSS ON DRYING: 0.5% max

Specification

The IUPAC name of L-Homophenylalanine is (2S)-2-amino-4-phenylbutanoic acid. With the CAS registry number 943-73-7, it is also named as (S)-alpha-Amino-benzenebutanoic acid. The product's categories are Phenylalanine Analogs and Other Aromatic alpha Amino Acids; API Intermediates; Homophenylalanine [Hph]; Amino Acids 13C, 2H, 15N; Chiral Compound; Amino Acids; Amino Acids & Derivatives; Aromatics. It is white solid which is stable under normal temperature and pressure. Additionally, this chemical should be sealed in the container and stored in the cool and dry place. When use it, people should not breathe dust and avoid contact with skin and eyes.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.53; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.97; (4)ACD/LogD (pH 7.4): -0.97; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 3; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 5; (12)Index of Refraction: 1.564; (13)Molar Refractivity: 50.12 cm3; (14)Molar Volume: 153.9 cm3; (15)Polarizability: 19.87×10-24 cm3; (16)Surface Tension: 51.1 dyne/cm; (17)Enthalpy of Vaporization: 59.84 kJ/mol; (18)Vapour Pressure: 9.79E-05 mmHg at 25°C; (19)Rotatable Bond Count: 4; (20)Exact Mass: 179.094629; (21)MonoIsotopic Mass: 179.094629; (22)Topological Polar Surface Area: 63.3; (23)Heavy Atom Count: 13; (24)Complexity: 164; (25)Defined Atom StereoCenter Count: 1.

Preparation of L-Homophenylalanine: It can be obtained by (R)-2-acetylamino-4-phenyl-butyric acid. This reaction needs reagent 6 N aq. HCl by heating. The yield is 96%.

Uses of L-Homophenylalanine: It is used as antitumor agent. It also can react with ethanol to get R-(-)-Homophenylalanin-ethylester. This reaction needs reagent HCl and Na2CO3. The yield is 89%.

People can use the following data to convert to the molecule structure.
1. SMILES:O=C(O)C(N)CCc1ccccc1
2. 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)
3. InChIKey:JTTHKOPSMAVJFE-UHFFFAOYAD