EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

laevo-isoleucine
(2S,3S)-2-amino-3-methylpentanoic acid

Supplier Sponsors

CAS Number: 73-32-5Picture of molecule3D/inchi
Other(deleted CASRN):1050482-26-2
ECHA EINECS - REACH Pre-Reg:200-798-2
FDA UNII: 04Y7590D77
Nikkaji Web:J2.818E
Beilstein Number:1721792
MDL:MFCD00064222
CoE Number:10482
XlogP3:-1.70 (est)
Molecular Weight:131.17501000
Formula:C6 H13 N O2
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:special dietary and nutritional additives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
JECFA Food Flavoring:2118 L-isoleucine
FEMA Number:4675 L-isoleucine
FDA:No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF):73-32-5 ; L-ISOLEUCINE
FDA Regulation:
FDA PART 172 -- FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION
Subpart D--Special Dietary and Nutritional Additives
Sec. 172.320 Amino acids.
 
Physical Properties:
Appearance:white powder (est)
Assay: 99.00 to 100.00
Food Chemicals Codex Listed: Yes
Melting Point: 287.00 to 288.00 °C. @ 760.00 mm Hg
Boiling Point: 225.77 °C. @ 760.00 mm Hg (est)
Vapor Pressure:0.031000 mmHg @ 25.00 °C. (est)
Flash Point: 194.00 °F. TCC ( 90.00 °C. )
logP (o/w): 0.799 (est)
Soluble in:
 water, 2.191e+004 mg/L @ 25 °C (est)
 water, 3.44E+04 mg/L @ 25 °C (exp)
 
Organoleptic Properties:
Odor Strength:none
Odor Description:odorless
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: antistatic agents
hair conditioning
skin conditioning
 
Suppliers:
AIDP
L-Isoleucine 98.5%-101.5%
Ajinomoto USA
AjiPure™ Isoleucine
Flavor: characteristic
Manufactured under cGMP conditions using no materials of animal origin.
Ajinomoto USA
isoLucine
Flavor: characteristic
L-isoleucine is one of the branched chain amino acids (L-isoleucine, L-valine, and L-leucine) and is classified as an essential amino acid. This means the body cannot manufacture L-isoleucine; it must be acquired through diet or supplementation. The male adult’s daily requirement is 10 mg per kg of body weight. Food sources for isoleucine include almonds, cashews and soy protein.
Alfa Biotechnology
For experimental / research use only.
L-Isoleucine 98%
Anhui Haibei
L-IsoLeucine
Atlantic Chemicals
L-isoLeucine
BOC Sciences
For experimental / research use only.
L-isoLeucine
Charkit Chemical
ISOLEUCINE, L-
EMD Millipore
For experimental / research use only.
L-isoLeucine
Foodchem International
L-isoLeucine
Glentham Life Sciences
L-Isoleucine, GlenCell?, suitable for cell culture
Glentham Life Sciences
L-isoLeucine
Graham Chemical
L-isoLeucine
Indis NV
For experimental / research use only.
L-Isoleucine
Jiangyin Healthway
L-isoleucine
New functional food ingredients
Penta International
L-ISOLEUCINE NATURAL
Penta International
L-ISOLEUCINE USP
Penta International
L-ISOLEUCINE
Prinova
L-isoLeucine FCC; USP
Sigma-Aldrich
L-Isoleucine, 99%, FCC, FG
Certified Food Grade Products
TCI AMERICA
For experimental / research use only.
L-isoLeucine >98.0%(T)
United International
L-Isoleucine Nat.
Zhong Ya Chemical
L-isoLeucine
 
Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
None - None found.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intraperitoneal-rat LD50 6822 mg/kg
LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Archives of Biochemistry and Biophysics. Vol. 58, Pg. 253, 1955.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
special dietary and nutritional additives
Recommendation for laevo-isoleucine usage levels up to:
 not for fragrance use.
 
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 25
Click here to view publication 25
 average usual ppmaverage maximum ppm
baked goods: 50.0000050.00000
beverages(nonalcoholic): 200.00000250.00000
beverages(alcoholic): 50.0000050.00000
breakfast cereal: 50.0000050.00000
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: --
fruit ices: --
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: --
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: 50.0000050.00000
milk products: 50.0000050.00000
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: 50.0000050.00000
sugar substitutes: --
sweet sauces: --
 
Safety References:
European Food Safety Authority (EFSA) reference(s):

Safety and efficacy of l-isoleucine produced by fermentation with Corynebacterium glutamicum KCCM 80189 for all animal species
View page or View pdf

Assessment of the application for renewal of authorisation of l-isoleucine produced by Escherichia coli FERM ABP-10641 as a nutritional additive, its extension of use in water for drinking and a new use as flavouring additive for all animal species
View page or View pdf

EPI System: View
ClinicalTrials.gov:search
Daily Med:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):73-32-5
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :6306
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
(2S,3S)-2-amino-3-methylpentanoic acid
Chemidplus:0000073325
RTECS:NR4705000 for cas# 73-32-5
 
References:
 (2S,3S)-2-amino-3-methylpentanoic acid
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:73-32-5
Pubchem (cid):6306
Pubchem (sid):134972796
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
CHEBI:View
CHEMBL:View
Golm Metabolome Database:Search
Metabolomics Database:Search
KEGG (GenomeNet):C00407
HMDB (The Human Metabolome Database):HMDB00172
FooDB:FDB012397
YMDB (Yeast Metabolome Database):YMDB00038
Export Tariff Code:2922.49.4050
FDA Listing of Food Additive Status:View
MedlinePlusSupp:View
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
 antistatic agents
 hair conditioning
 skin conditioning
 
Occurrence (nature, food, other):note
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 rosemary leaf
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 soybean shoot
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 spearmint leaf
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Synonyms:
 ajipure isoleucine
(2S,3S)-2-amino-3-methyl pentanoic acid
(2S,3S)-2-amino-3-methyl-pentanoic acid
(2S,3S)-2-amino-3-methylpentanoic acid
[S-(R*,R*)]-2-amino-3-methylpentanoic acid
(2S,3S)-a-amino-b-methyl-N-valeric acid
(2S,3S)-a-amino-b-methylvaleric acid
(2S,3S)-alpha-amino-beta-merthyl valeric acid
(2S,3S)-alpha-amino-beta-methyl-N-valeric acid
L-isoleucin
(S,S)-isoleucine
(S)-isoleucine
2S,3S-isoleucine
L-isoleucine
L-isoleucine FCC; USP
L-isoleucine natural
isoleucine, L-
 pentanoic acid, 2-amino-3-methyl-, (2S,3S)-
 

Articles:

PubMed:Effects of fenugreek (Trigonella foenum-graecum L.) seed on bone mechanical properties in rats.
Leffingwell & Associates:Flavor Properties of FEMA GRAS List 25 flavor chemicals
PubMed:ZnCl2-mediated practical protocol for the synthesis of Amadori ketoses.
PubMed:Gustatory responsiveness to the 20 proteinogenic amino acids in the spider monkey (Ateles geoffroyi).
PubMed:Hydrolysis of wheat gluten by combining peptidases of Flammulina velutipes and electrodialysis.
PubMed:Expression of NAD(H) kinase and glucose-6-phosphate dehydrogenase improve NADPH supply and L-isoleucine biosynthesis in Corynebacterium glutamicum ssp. lactofermentum.
PubMed:L-Leucine and L-isoleucine enhance growth of BBN-induced urothelial tumors in the rat bladder by modulating expression of amino acid transporters and tumorigenesis-associated genes.
PubMed:A dipeptide and an amino acid present in whey protein hydrolysate increase translocation of GLUT-4 to the plasma membrane in Wistar rats.
PubMed:Increasing l-isoleucine production in Corynebacterium glutamicum by overexpressing global regulator Lrp and two-component export system BrnFE.
PubMed:[Overexpression of Corynebacterium glutamicum NAD kinase improves L-isoleucine biosynthesis].
PubMed:Zn(2+) and L-isoleucine induce the expressions of porcine β-defensins in IPEC-J2 cells.
PubMed:Long-term treatment with L-isoleucine or L-leucine in AIN-93G diet has promoting effects on rat bladder carcinogenesis.
PubMed:Co-expression of feedback-resistant threonine dehydratase and acetohydroxy acid synthase increase L-isoleucine production in Corynebacterium glutamicum.
PubMed:Overexpression of NAD kinases improves the L-isoleucine biosynthesis in Corynebacterium glutamicum ssp. lactofermentum.
PubMed:Purification and structure analysis of mycolic acids in Corynebacterium glutamicum.
PubMed:Leucine is essential for attenuating fetal growth restriction caused by a protein-restricted diet in rats.
PubMed:Gelatin enhances 2-keto-L-gulonic acid production based on Ketogulonigenium vulgare genome annotation.
PubMed:Metabolic pathways and fermentative production of L-aspartate family amino acids.
PubMed:Heating improves poor compliance with branched chain amino acid-rich supplementation in patients with liver cirrhosis: A before-after pilot study.
PubMed:Inhibitory effect of aroma on the bitterness of branched-chain amino acid solutions.
PubMed:Pathway analysis of branched-chain ester biosynthesis in apple using deuterium labeling and enantioselective gas chromatography-mass spectrometry.
PubMed:Sequence diversity of the peptaibol antibiotic suzukacillin-A from the mold Trichoderma viride.
PubMed:Effect of individual amino acids and glucose on activation and germination of Rhizopus oligosporus sporangiospores in tempe starter.
PubMed:Lack of carcinogenicity of L-isoleucine in F344/DuCrj rats.
PubMed:Clinical comparison of branched-chain amino acid (l-Leucine, l-Isoleucine, l-Valine) granules and oral nutrition for hepatic insufficiency in patients with decompensated liver cirrhosis (LIV-EN study).
PubMed:Suppression of the bitterness of enteral nutrients using increased particle sizes of branched-chain amino acids (BCAAs) and various flavours: a taste sensor study.
PubMed:Industrial production of amino acids by coryneform bacteria.
PubMed:Biosynthesis of strawberry aroma compounds through amino acid metabolism.
PubMed:Effects of copper and zinc on growth, feeding and oxygen consumption of Farfantepenaeus paulensis postlarvae (Decapoda: Penaeidae).
PubMed:Olfactory discrimination of amino acids in brown bullhead catfish.
PubMed:Response of rainbow trout (Oncorhynchus mykiss) to supplements of individual essential amino acids in a semipurified diet, including an estimate of the maintenance requirement for essential amino acids.
PubMed:Subchronic toxicity study of L-isoleucine in F344 rats.
PubMed:Timing and dose of amino acids injected into prepyriform cortex influence food intake.
PubMed:Performance and nutrient balance in growing swine fed low-protein diets supplemented with amino acids and potassium.
PubMed:Methylmalonic acid concentrations in serum of normal subjects: biological variability and effect of oral L-isoleucine loads before and after intramuscular administration of cobalamin.
PubMed:Effects of valine on 15N incorporation into serum and tissue protein and non-protein fractions following 15N-L-leucine administration to normal and liver-injured rats.
PubMed:Comparative effects of individual amino acid excesses when added to a corn-soybean meal diet: effects on growth and dietary choice in the chick.
PubMed:The inducer of the feeding response in Penaeus paulensis (Crustacea-Decapoda).
PubMed:Production of oxytetracycline by Streptomyces rimosus 12,907 as an animal feed supplement.
 
Notes:
an essential branched-chain aliphatic amino acid found in many proteins. it is an isomer of leucine. it is important in hemoglobin synthesis and regulation of blood sugar and energy levels. Dietary supplement, nutrient Branched chain amino acids (BCAA) are essential amino acids whose carbon structure is marked by a branch point. These three amino acids are critical to human life and are particularly involved in stress, energy and muscle metabolism. BCAA supplementation as therapy, both oral and intravenous, in human health and disease holds great promise. "BCAA" denotes valine, isoleucine and leucine which are branched chain essential amino acids. Despite their structural similarities, the branched amino acids have different metabolic routes, with valine going solely to carbohydrates, leucine solely to fats and isoleucine to both. The different metabolism accounts for different requirements for these essential amino acids in humans: 12 mg/kg, 14 mg/kg and 16 mg/kg of valine, leucine and isoleucine respectively. Furthermore, these amino acids have different deficiency symptoms. Valine deficiency is marked by neurological defects in the brain, while isoleucine deficiency is marked by muscle tremors. BCAA are decreased in patients with liver disease, such as hepatitis, hepatic coma, cirrhosis, extrahepatic biliary atresia or portacaval shunt; They provide ingredients for the manufacturing of other essential biochemical components in the body, some of which are utilized for the production of energy, stimulants to the upper brain and helping you to be more alert.; aromatic amino acids (AAA)-tyrosine, tryptophan and phenylalanine, as well as methionine-are increased in these conditions. Valine, in particular, has been established as a useful supplemental therapy to the ailing liver. All the BCAA probably compete with AAA for absorption into the brain. Supplemental BCAA with vitamin B6 and zinc help normalize the BCAA:AAA ratio. The BCAA are not without side effects. Leucine alone, for example, exacerbates pellagra and can cause psychosis in pellagra patients by increasing excretion of niacin in the urine. Leucine may lower brain serotonin and dopamine. A dose of 3 g of isoleucine added to the niacin regime has cleared leucine-aggravated psychosis in schizophrenic patients. Isoleucine may have potential as an antipsychotic treatment. Leucine is more highly concentrated in foods than other amino acids. A cup of milk contains 800 mg of leucine and only 500 mg of isoleucine and valine. A cup of wheat germ has about 1.6 g of leucine and 1 g of isoleucine and valine. The ratio evens out in eggs and cheese. One egg and an ounce of most cheeses each contain about 400 mg of leucine and 400 mg of valine and isoleucine. The ratio of leucine to other BCAA is greatest in pork, where leucine is 7 to 8 g and the other BCAA together are only 3 to 4 g. (http://www.dcnutrition.com)
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