CAS 319-78-8 D-Isoleucine (HCID 76551)

Overview

D-isoleucine is the D-enantiomer of isoleucine. It has a role as a Saccharomyces cerevisiae metabolite and a bacterial metabolite. It is a D-alpha-amino acid and an isoleucine. It is a conjugate base of a D-isoleucinium. It is a conjugate acid of a D-isoleucinate. It is an enantiomer of a L-isoleucine. It is a tautomer of a D-isoleucine zwitterion.

Names & identifiers

Preferred name: D-Isoleucine
IUPAC: (2R,3R)-2-amino-3-methylpentanoic acid
English name: (2R,3R)-2-Amino-3-methylpentanoic acid
Molecular formula: C6H13NO2
Molecular weight: 131.17

Names & synonyms

D-IsoleucineIsoleucine, D-(R)-Isoleucine(2R,3R)-2-Amino-3-methylvaleric acidUNII-V87GJA0G54V87GJA0G54DTXSID1046346EINECS 206-269-2BRN 1721793ISOLEUCINE, (-)-CHEBI:277304-04-00-02774 (Beilstein Handbook Reference)

Show more names

D-IleH-D-ILE-OHD-Ile-OHd-isoleucinD-IsoLD-lle-OHH-D-lle-OHD-lsoleucine

(R)-2-Amino-(S)-3-methylvaleric acid(R)IsoleucineRefChem:130638DTXCID701477645(2R, 3R)2Amino3methylpentanoic acid19764-31-9319-78-8(2R,3R)-2-amino-3-methylpentanoic acid

Database identifiers

CAS: 319-78-8
PubChem CID: 76551
DTXSID: DTXSID1046346
ChEBI: CHEBI:27730
UNII: V87GJA0G54
EC Number: 206-269-2
Nikkaji: J9.187A

Properties

Computed structural properties

XLogP: -1.7
Topological polar surface area: 63.3 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 3
Rotatable bonds: 3
Heavy atoms: 9
Formal charge: 0
Complexity: 103

Experimental & physicochemical properties

Chemical Classes · 2 items

Biological Agents -> Amino Acids and Derivatives

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

Flavoring AgentsEU Flavoring substances

Solubility · 2 items

Soluble in water; Insoluble in ether

Insoluble (in ethanol)

Vapor Pressure0.00000001 [mmHg]

Physical Description · 3 items

Solid; [Sigma-Aldrich MSDS]

Glistening solid; [Merck Index] White powder; [Sigma-Aldrich MSDS]

White crystalline powder; odourless

Physicochemical properties

Melting point: 272 · 272-274 °C
alpha: -37 · -37 º (c=5, 1 N HCl 24 ºC)
Boiling point: 225.8 · 225.8±23.0 °C(Predicted)
Density: 1.172 · 1.1720 (estimate)
refractive index: -40.5 ° · -40.5 ° (C=4, 6mol/L HCl)
storage temp.: Sealed in dry,Room Temperature
solubility: Aqueous Acid (Slightly), Water (Slightly)
pka: 2.57 · 2.57±0.24(Predicted)
form: Solid
color: White to Off-White
Major Application: cell analysis
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
InChIKey: AGPKZVBTJJNPAG-RFZPGFLSSA-N
SMILES: C(O)(=O)[C@@H]([C@H](C)CC)N
CAS DataBase Reference: 319 · 319-78-8(CAS DataBase Reference)
FDA UNII: 87 GJA0G54 · V87GJA0G54
EPA Substance Registry System: D-Isoleucine (319-78-8)
UNSPSC Code: 12352209 · 12352209
NACRES: 26 · NA.26
Hazard Codes: Xn
Risk Statements: 40 · 40
Safety Statements: 24 · 24/25-36-22
WGK Germany: 3 · 3
RTECS: 4700000 · NR4700000
HS Code: 29224995 · 29224995
Storage Class: 11 · 11 - Combustible Solids
Toxicity: 50 · 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.

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 100% (104 of 104) of all reports.

Not Classified

Aggregated GHS information provided per 104 reports by companies from 1 notifications to the ECHA C&L Inventory.

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 3 items

Chemical: DL-Isoleucine

Regulation (EC) No 1831/2003 (amended)

Isoleucine: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - DL-Isoleucine: Environment tier I assessment

Hazards Summary · 2 items

Causes altered sleep time (including change in righting reflex), dyspnea, and decreased body temperature in intraperitoneal lethal-dose studies of rats (LD50 = 6,822 mg/kg); [RTECS]

Safe when used as a flavoring agent in food; [JECFA] May cause irritation; [Sigma-Aldrich MSDS]

Hazard Classes and Categories · 2 items

Not Classified

Skin Irrit. 2 (100%)

Safety data

wgk: 3
rtecs: NR4700000
hs_code: 29224995
Toxicity: 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.
risk_code: 40
hazard_code: Xn
safety_code: 24/25-36-22
Storage Class: 11 - Combustible Solids

Chemistry & industry

Uses & manufacturing

Uses · 3 items

Isoleucine is an essential amino acid; [Merck Index]

Isoleucine is an essential amino acid; [Merck Index] Used as a flavoring agent; [FDA] Used in animal feeds; [ExPub: EFSA]

Farming (Feed Additives) [Category: Industry]

Use ClassificationFlavoring Agents -> JECFA Flavorings Index

General Manufacturing InformationIsoleucine: ACTIVE

Applications

UsesMay contain up to 10% allo-isomer.

UsesD-Isoleucine is not biosynthesized in the human body and is therefore categorized as an essential amino acid that must be obtained through diet. It is also an important building block that is used in the formation of hemoglobin in humans.