D-Isoleucine supplier | CasNO.319-78-8

Name
(2R,3R)-2-Amino-3-methylpentanoic acid
EINECS 206-269-2
CAS No. 319-78-8
Article Data88
CAS DataBase
Density 1.035 g/cm³
Solubility
Melting Point 272-274 °C
Formula C₆H₁₃NO₂
Boiling Point 297.8 °C at 760 mmHg
Molecular Weight 131.175
Flash Point 109.2 °C
Transport Information
Appearance white to very slightly yellow powder
Safety 24/25-36-22
Risk Codes 40
Molecular Structure
Hazard Symbols Xn
Synonyms Isoleucine,D- (8CI);(R)-Isoleucine;(2R,3R)-2-Amino-3-methylpentanoic acid;
PSA 63.32000
LogP 1.14470

Synthetic route

: 73-32-5, 319-78-8, 443-79-8, 1509-34-8, 1509-35-9, 3107-04-8, 7004-09-3
isoleucine

A: 1509-34-8
D-allo-isoleucine

B: 319-78-8
D-Isoleucine

Conditions

Conditions	Yield
With C13H15NO5V(1-)*C16H36N(1+) In ethanol; water	A 32% B n/a
With C13H15NO5V(1-)*C16H36N(1+) In ethanol; water	A n/a B 22%

: 73-32-5, 319-78-8, 443-79-8, 1509-34-8, 1509-35-9, 3107-04-8, 7004-09-3
DL-isoleucine

: 319-78-8
D-Isoleucine

Conditions

Conditions	Yield
durch Einw. von gaerender Hefe;
crystallization with L-Phe (1:2 ratio) from water-ethanol (pH 5-6) at 25 deg C;
Multi-step reaction with 2 steps 2: brucine / man zerlegt in die optisch aktiven Komponenten und erwaermt mit 10prozentiger Salzsaeure auf dem Wasserbad View Scheme

: 21582-41-2
(-)(2S:3R)-2-bromo-3-methyl-valeric acid

: 319-78-8
D-Isoleucine

Conditions

Conditions	Yield
bei Ueberfuehrung in das (Carboxymetyl)-amid, folgender Aminierung und Hydrolyse;

: 4101-35-3, 89810-44-6
N-formyl-isoleucine

: 319-78-8
D-Isoleucine

Conditions

Conditions	Yield
With brucine man zerlegt in die optisch aktiven Komponenten und erwaermt mit 10prozentiger Salzsaeure auf dem Wasserbad;
With brucine man zerlegt in die optisch aktiven Komponenten und erwaermt mit 20prozentiger Bromwasserstoffsaeure;

: 907582-55-2
N-formyl-D-isoleucine

: 319-78-8
D-Isoleucine

Conditions

Conditions	Yield
With hydrogen bromide

: 19764-31-9
(2R,3R)-2-acetamido-3-methylpentanoic acid

: 319-78-8
D-Isoleucine

Conditions

Conditions	Yield
With hydrogenchloride
With Escherichia coli D-aminoacylase amano In phosphate buffer at 37℃; for 12h; pH=8.0;
Stage #1: (2R,3R)-2-acetamido-3-methylpentanoic acid With hydrogenchloride; water at 80℃; Stage #2: With triethylamine

: 868-28-0
N-D-isoleucyl-glycine

A: 319-78-8
D-Isoleucine

B: 56-40-6
glycine

Conditions

Conditions	Yield
Hydrolysis;

: 907582-60-9
N-chloroacetyl-D-isoleucine

: 319-78-8
D-Isoleucine

Conditions

Conditions	Yield
With hydrogenchloride

: 73-32-5, 319-78-8, 443-79-8, 1509-34-8, 1509-35-9, 3107-04-8, 7004-09-3
DL-isoleucine

A: 73-32-5
L-isoleucine

B: 319-78-8
D-Isoleucine

: 73-32-5
L-isoleucine

: 319-78-8
D-Isoleucine

Conditions

Conditions	Yield
With hydrogenchloride; ethanethiol at 110℃; Rate constant; various times;

: 2627-86-3
(S)-1-phenyl-ethylamine

: 2-methyl-4-sec-butylidene-5-oxazolone

A: 1509-34-8
D-allo-isoleucine

B: 73-32-5
L-isoleucine

C: 319-78-8
D-Isoleucine

D: 1509-35-9
D-alloisoleucine

Conditions

Conditions	Yield
Product distribution; Rate constant; multistep reaction;

...Expand

: 106749-12-6
(2S,3R)-2-Azido-3-methyl-pentanoic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

A: 1509-34-8
D-allo-isoleucine

B: 73-32-5
L-isoleucine

C: 319-78-8
D-Isoleucine

D: 1509-35-9
D-alloisoleucine

Conditions

Conditions	Yield
With titanium tetrakis(benzyl alkoxide); hydrogen; Pd-BaSO4 1.) benzyl alcohol, 130 gradC 2.) EtOH, EtOAc, 1 atm, r.t.; Yield given. Multistep reaction. Title compound not separated from byproducts;

...Expand

: 76569-26-1
1-p-chlorophenylsulphonylimino-2,3-dihydro-9-methyl-1H-pyrrolo<1,2-a>indole

A: 3285-00-5
dihydro-5-butyl-5-methyl-2-(3H)-furanone

B: 7011-83-8, 187600-82-4
5-hexyl-5-methyldihydro-2(3H)-furanone

C: 319-78-8
D-Isoleucine

D: 63-91-2
L-phenylalanine

Conditions

Conditions	Yield
With hydrogenchloride; beauverolide Ka; D-amino-acid oxidase; sodium pyrophosphate buffer 1.) 110 deg C, 3 d, 2.) 38 deg C, 1 h; Multistep reaction;

...Expand

: 76569-26-1
1-p-chlorophenylsulphonylimino-2,3-dihydro-9-methyl-1H-pyrrolo<1,2-a>indole

A: 319-78-8
D-Isoleucine

B: 63-91-2
L-phenylalanine

Conditions

Conditions	Yield
With phosphate buffer; beauverolide Ka; D-amino-acidoxidase; toluene-4-sulfonic acid 1.) 110 deg C, 20 h, 2.)38 deg C, 2 h; Multistep reaction;

: 76569-26-1
1-p-chlorophenylsulphonylimino-2,3-dihydro-9-methyl-1H-pyrrolo<1,2-a>indole

A: 319-78-8
D-Isoleucine

B: 63-91-2
L-phenylalanine

C: 73-22-3
L-Tryptophan

Conditions

Conditions	Yield
With phosphate buffer; beauverolide Ka; D-amino-acidoxidase; toluene-4-sulfonic acid 1.) 110 deg C, 20 h, 2.)38 deg C, 2 h; Multistep reaction;

...Expand

: 104068-43-1
3-sec-butyl-6-isopropyl-piperazine-2,5-dione

: 10035-10-6, 12258-64-9
hydrogen bromide

A: 640-68-6
D-Val-OH

B: 319-78-8
D-Isoleucine

Conditions

Conditions	Yield
at 115 - 120℃;

...Expand

active α-bromo-β-methyl-β-ethyl-propionic acid: active α-bromo-β-methyl-β-ethyl-propionic acid

: 319-78-8
D-Isoleucine

Conditions

Conditions	Yield
With ammonia; water at 37℃;

bituminous peat: bituminous peat

A: 61-90-5
L-leucine

B: 319-78-8
D-Isoleucine

Conditions

Conditions	Yield
With sulfuric acid

: 74-90-8
hydrogen cyanide

: 1730-97-8
(S)-2-methylbutyraldehyde

: 7664-41-7
ammonia

A: 319-78-8
D-Isoleucine

B: 1509-35-9
D-alloisoleucine

Conditions

Conditions	Yield
Verseifen des entstandenen Aminovaleronitrils;

...Expand

: 868-28-0
N-isoleucyl-glycine

sulfuric acid (25 percent ): sulfuric acid (25 percent )

A: 319-78-8
D-Isoleucine

B: 56-40-6
glycine

Conditions

Conditions	Yield
-glycine;

...Expand

: 106749-13-7
(R)-3-Methyl-pentanoic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

: 319-78-8
D-Isoleucine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 67 percent / LDA, Me3SiCl, NBS 2: 93 percent / NaN3 / dimethylformamide / 60 h / Ambient temperature 3: 1.) Ti(OCH2Ph)4 2.) H2 / 2.) Pd/BaSO4 / 1.) benzyl alcohol, 130 gradC 2.) EtOH, EtOAc, 1 atm, r.t. View Scheme

: 106749-11-5
(2R,3R)-2-Bromo-3-methyl-pentanoic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

: 319-78-8
D-Isoleucine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / NaN3 / dimethylformamide / 60 h / Ambient temperature 2: 1.) Ti(OCH2Ph)4 2.) H2 / 2.) Pd/BaSO4 / 1.) benzyl alcohol, 130 gradC 2.) EtOH, EtOAc, 1 atm, r.t. View Scheme

: 319-78-8, 443-79-8, 1509-34-8, 1509-35-9, 3107-04-8, 7004-09-3, 73-32-5
isoleucine

A: 73-32-5
L-isoleucine

B: 319-78-8
D-Isoleucine

Conditions

Conditions	Yield
With shaking calcined L-Pro chiral ordered mesoporous silica Resolution of racemate;
With R-(3,3'-dibromo-1,1'-binaphthyl)-20-crown-6 coated C18 silica gel column at 25℃; pH=2; Resolution of racemate;
With capillary electrochromatography open-tubular column coated with 1-allylimidazolium-β-cyclodextrin In aq. acetate buffer at 20℃; pH=8; pH-value; Resolution of racemate;

: 1356449-88-1
calyxamide B

A: 56-41-7
L-alanin

B: 515-94-6, 1915-96-4, 4033-39-0, 6018-54-8
(S)-2,3-diaminopropionic acid

C: 73-32-5
L-isoleucine

D: 319-78-8
D-Isoleucine

E: 56-85-9
L-glutamine

Conditions

Conditions	Yield
Stage #1: calyxamide B With dihydrogen peroxide; sodium hydroxide at 65℃; for 0.666667h; Stage #2: With hydrogenchloride; water at 110℃; for 24h;

...Expand

: 1444002-12-3
cyclo-(-L-Ile-D-Ile-L-Lys-L-Ile-D-Phe-D-Leu-L-Ile-D-Ala-)

A: 338-69-2
D-Alanine

B: 328-38-1
(R)-leucine

C: 73-32-5
L-isoleucine

D: 319-78-8
D-Isoleucine

E: 56-87-1
L-lysine

F: 673-06-3
D-(R)-phenylalanine

Conditions

Conditions	Yield
With hydrogenchloride In water at 110℃;

...Expand

: 1444002-14-5
surugamides C

A: 338-69-2
D-Alanine

B: 72-18-4
L-valine

C: 328-38-1
(R)-leucine

D: 73-32-5
L-isoleucine

E: 319-78-8
D-Isoleucine

F: 56-87-1
L-lysine

G: 673-06-3
D-(R)-phenylalanine

Conditions

Conditions	Yield
With hydrogenchloride In water at 110℃;

...Expand

: 1444002-15-6
surugamides D

A: 338-69-2
D-Alanine

B: 72-18-4
L-valine

C: 328-38-1
(R)-leucine

D: 73-32-5
L-isoleucine

E: 319-78-8
D-Isoleucine

F: 56-87-1
L-lysine

G: 673-06-3
D-(R)-phenylalanine

Conditions

Conditions	Yield
With hydrogenchloride In water at 110℃;

...Expand

: 1444002-16-7
surugamides E

A: 338-69-2
D-Alanine

B: 72-18-4
L-valine

C: 328-38-1
(R)-leucine

D: 73-32-5
L-isoleucine

E: 319-78-8
D-Isoleucine

F: 56-87-1
L-lysine

G: 673-06-3
D-(R)-phenylalanine

Conditions

Conditions	Yield
With hydrogenchloride In water at 110℃;

...Expand

: 1509-34-8
D-allo-isoleucine

: 319-78-8
D-Isoleucine

Conditions

Conditions	Yield
With ammonium metavanadate; salicylaldehyde; sodium hydroxide In water for 6h; pH=11; Reflux;

: 319-78-8
D-Isoleucine

: 117-08-8
tetrachlorophthalic anhydride

: TCP-D-Ile-OH

Conditions

Conditions	Yield
In N,N-dimethyl-formamide Microwave irradiation;	98%

: 319-78-8
D-Isoleucine

: 383-63-1
ethyl trifluoroacetate,

: (2R,3R)-3-methyl-2-(2,2,2-trifluoroacetamido)pentanoic acid

Conditions

Conditions	Yield
With triethylamine In methanol at 20℃; for 24h;	96%

: 319-78-8
D-Isoleucine

: 2-((tert-butoxycarbonyloxy)imino)-2-phenylacetonitrile

: 55721-65-8
Boc-D-Ile-OH

Conditions

Conditions	Yield
With triethylamine In water; acetone for 5h; Ambient temperature;	95%

: 319-78-8
D-Isoleucine

: 94318-70-4
(2R,3R)-2-bromo-3-methylpentanoic acid

Conditions

Conditions	Yield
With hydrogen bromide; sodium nitrite In water at 0 - 20℃; for 16h;	95%
With hydrogen bromide; potassium bromide; sodium nitrite Substitution;
With hydrogen bromide; sodium nitrite In water at 0 - 20℃; for 16h;

: 319-78-8
D-Isoleucine

: 488-15-3, 51576-04-6, 59653-35-9, 70748-47-9, 86630-77-5, 86540-81-0
(2R,3R)-2-hydroxy-3-methylpentanoic acid

Conditions

Conditions	Yield
With sulfuric acid; sodium nitrite	93%
Stage #1: D-Isoleucine With sodium nitrite In water Stage #2: With sulfuric acid; water	85%
With hydrogenchloride; acetic acid; sodium nitrite

: 319-78-8
D-Isoleucine

: 78569-22-9
3-(N-benzyloxycarbonyl-L-leucyl)-1,3-thiazolidine-2-thione

: 78569-25-2
Z-L-Leu-D-Ileu-OH

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran; water Ambient temperature;	89%

: 10228-90-7
9-methoxyacridine

: 319-78-8
D-Isoleucine

: (2R,3R)-2-(Acridin-9-ylamino)-3-methyl-pentanoic acid

Conditions

Conditions	Yield
In methanol for 10h; Heating;	80%

: 319-78-8
D-Isoleucine

: azido-D-Ile

Conditions

Conditions	Yield
With triflic azide; potassium carbonate; copper(II) sulfate In methanol; dichloromethane; water at 20℃;	73%
Stage #1: D-Isoleucine With triflic azide; potassium carbonate; copper(II) sulfate; potassium hydroxide In methanol; water for 8h; pH=8 - 10; Stage #2: With sulfuric acid In water pH=3.5;

: 319-78-8
D-Isoleucine

: 2-chloro-6-(naphthalen-2-yl)-4-phenylpyridine-3-carbonitrile

: 2-[3-cyano-6-(2-naphthyl)-4-phenylpyridin-2-ylamino]-3-methylpentanoic acid

Conditions

Conditions	Yield
With sodium carbonate In ethanol; water at 100℃; for 8h; pH=9 - 9.5;	53%

: 319-78-8
D-Isoleucine

: 104-15-4
toluene-4-sulfonic acid

: 100-51-6
benzyl alcohol

: 80174-45-4
D-isoleucine benzyl ester p-toluenesulfonate

Conditions

Conditions	Yield
In benzene at 70 - 115℃; for 5h; Dean-Stark;	46%

...Expand

: 319-78-8
D-Isoleucine

: 53406-00-1
3-carbamoyl-1-(2,4-dinitrophenyl)pyridinium chloride

: C12H17N2O3(1+)

Conditions

Conditions	Yield
With triethylamine In methanol at 20℃; for 24h;	35.2%

: 319-78-8
D-Isoleucine

: 31010-69-2
7-methoxycarbonylpterin

: (2R,3R)-2-(2-amino-4-oxo-3,4-dihydropteridine-7-carboxamido)-3-methylpentanoic acid

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 20℃;	19%

: 57-48-7
D-Fructose

: 319-78-8
D-Isoleucine

: (R)-4-((R)-sec-butyl)-3-oxo-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbaldehyde

Conditions

Conditions	Yield
With acetic acid; triethylamine at 80℃; for 8h;	15.1%

: 67-56-1
methanol

: 319-78-8
D-Isoleucine

: 2577-46-0, 18869-44-8, 42271-58-9, 81084-74-4, 107998-45-8, 118878-53-8
D-Isoleucine methyl ester

Conditions

Conditions	Yield
With hydrogenchloride
With hydrogenchloride at 100℃; for 0.5h;
With chloro-trimethyl-silane

: 7148-74-5, 22592-73-0, 71425-59-7, 52152-04-2
(R)-2-bromopropionyl chloride

: 319-78-8
D-Isoleucine

: N-(2-bromo-propionyl)-isoleucine

Conditions

Conditions	Yield
With sodium hydroxide; diethyl ether ;

: 28659-88-3, 59960-79-1, 104420-63-5
(R)-2-Bromo-4-methyl-pentanoyl chloride

: 319-78-8
D-Isoleucine

: 909874-75-5
N-(2-bromo-4-methyl-valeryl)-isoleucine

Conditions

Conditions	Yield
With sodium hydroxide unter Eiskuehlung; ;

: 319-78-8
D-Isoleucine

: 1460-34-0
2-oxo-3(RS)-methylvaleric acid

Conditions

Conditions	Yield
Aerobe oxydative Desaminierung unter der Einwirkung von D-Aminosaeure-Oxydase-Praeparaten aus tierischen Organen;

: 319-78-8
D-Isoleucine

: 1565-80-6
(2S)-2-methyl-1-butanol

Conditions

Conditions	Yield
With Sucrose durch Reinzuchthefe;

: 319-78-8
D-Isoleucine

: 1730-91-2
(S)-2-Methylbutyric acid

Conditions

Conditions	Yield
durch Einw. von Faeulnisbakterien;

: 319-78-8
D-Isoleucine

: 1730-92-3
(3S)-methylvaleric acid

Conditions

Conditions	Yield
durch Einw. von Faeulnisbakterien;

: 319-78-8
D-Isoleucine

: 319-78-8, 443-79-8, 1509-34-8, 1509-35-9, 3107-04-8, 7004-09-3, 73-32-5
isoleucine

Conditions

Conditions	Yield
With barium dihydroxide at 180℃; aus dem enthaltenen Gemisch von d-Isoleucin und d-Alloisoleucin entfernt man das erstere durch Vergaeren mit Hefe in Gegenwart von Zucker; d-alloisoleucine;

: 319-78-8
D-Isoleucine

: 61748-89-8
(R)-3-methyl-2-oxovaleric acid

Conditions

Conditions	Yield
With enzyme-substance from pig's kidney

: 319-78-8
D-Isoleucine

: 4101-35-3, 89810-44-6
N-formyl-isoleucine

Conditions

Conditions	Yield
durch Formylierung; formyl-d-isoleucine;

: 319-78-8
D-Isoleucine

A: 96-15-1
2-Methylbutylamine

B: 35590-81-9, 35712-77-7, 39897-59-1, 142698-73-5, 142698-74-6
3,6-di-sec-butyl-piperazine-2,5-dione

: 319-78-8
D-Isoleucine

: 33204-49-8
(R)-2-methyl-butyraldehyde-(2,4-dinitro-phenylhydrazone)

: 319-78-8
D-Isoleucine

: 7407-67-2, 63905-57-7, 100937-49-3
N-[(2,4-dichloro-phenoxy)-acetyl]-D-isoleucine

D-Isoleucine Specification

The CAS registry number of D-Isoleucine is 319-78-8. In addition, the molecular formula is C₆H₁₃NO₂ and the molecular weight is 131.17. The IUPAC name is (2R,3R)-2-amino-3-methylpentanoic acid. What's more, it is a kind of white to very slightly yellow powder. Besides it can be used in biochemical research and as nutritional supplements in medicine.

Physical properties about D-Isoleucine are: (1)ACD/LogP: 0.73; (2)ACD/LogD (pH 5.5): -1.77; (3)ACD/LogD (pH 7.4): -1.77; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 3; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 4; (11)Polar Surface Area: 29.54 Å²; (12)Index of Refraction: 1.462; (13)Molar Refractivity: 34.86 cm³; (14)Molar Volume: 126.6 cm³; (15)Polarizability: 13.82 ×10^-24cm³; (16)Surface Tension: 39 dyne/cm; (17)Density: 1.035 g/cm³; (18)Flash Point: 90.3 °C; (19)Enthalpy of Vaporization: 50.93 kJ/mol; (20)Boiling Point: 225.8 °C at 760 mmHg; (21)Vapour Pressure: 0.0309 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
During using it, wear suitable protective clothing and avoid contact with skin and eyes. In addition, do not breathe dust. There is limited evidence of a carcinogenic effect.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)[C@H](N)[C@H](C)CC
(2)Std.InChI: InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5-/m1/s1
(3)Std.InChIKey: AGPKZVBTJJNPAG-RFZPGFLSSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LD50	intraperitoneal	6822mg/kg (6822mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) LUNGS, THORAX, OR RESPIRATION: DYSPNEA	Archives of Biochemistry and Biophysics. Vol. 64, Pg. 319, 1956.

Product Name

(2R,3R)-2-Amino-3-methylpentanoic acid

Synthetic route

D-Isoleucine Specification

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