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

laevo-citrulline
delta-ureidonorvaline

Supplier Sponsors

CAS Number: 372-75-8Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:206-759-6
FDA UNII: 29VT07BGDA
Nikkaji Web:J5.711H
Beilstein Number:1725416
MDL:MFCD00064397
XlogP3:-4.30 (est)
Molecular Weight:175.18821000
Formula:C6 H13 N3 O3
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
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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
 
Physical Properties:
Appearance:white powder (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 235.50 °C. @ 760.00 mm Hg
Boiling Point: 386.00 to 387.00 °C. @ 760.00 mm Hg (est)
Flash Point: 370.00 °F. TCC ( 187.70 °C. ) (est)
logP (o/w): -3.190
Soluble in:
 water, 1.283e+004 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: skin conditioning
 
Suppliers:
AIDP
L-Citrulline
Alfa Biotechnology
For experimental / research use only.
L-(+)Citrulline 98%
Atlantic Chemicals
L-Citrulline
AuNutra® Industries
L-Citrulline
BOC Sciences
For experimental / research use only.
L-CITRULLINE (5-13C, 99%; 4,4,5,5-D4, 95%) >98%
ExtraSynthese
For experimental / research use only.
L-Citrulline
Glentham Life Sciences
L-Citrulline
Graham Chemical
L-Citrulline
Indis NV
For experimental / research use only.
L-Citrulline
Penta International
L-CITRULLINE
Prinova
L-Citrulline
Qingdao Dacon Trading
L-Citrulline
Sigma-Aldrich: Sigma
For experimental / research use only.
L-Citrulline ≥98% (TLC)
United International
L-Citrulline
 
Safety Information:
Preferred SDS: View
 
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:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
special dietary and nutritional additives
Recommendation for laevo-citrulline usage levels up to:
 not for fragrance use.
 
Recommendation for laevo-citrulline flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):372-75-8
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :9750
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(2S)-2-amino-5-(carbamoylamino)pentanoic acid
Chemidplus:0000372758
 
References:
 (2S)-2-amino-5-(carbamoylamino)pentanoic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):9750
Pubchem (sid):134974821
 
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
CHEBI:View
CHEMBL:View
Golm Metabolome Database:Search
Metabolomics Database:Search
KEGG (GenomeNet):C00327
HMDB (The Human Metabolome Database):HMDB00904
FooDB:FDB011841
YMDB (Yeast Metabolome Database):YMDB00060
Export Tariff Code:2924.10.1050
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:
 biological additives
 
Occurrence (nature, food, other):note
 apple custard apple fruit
Search Trop Picture
 cantaloupe fruit
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 chayote plant
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 cucumber fruit
Search Trop Picture
 garlic bulb
Search Trop Picture
 irish moss thallus
Search PMC Picture
 melon bitter melon fruit
Search Trop Picture
 sesame
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 soursop plant
Search Trop Picture
 watermelon fruit
Search Trop Picture
 
Synonyms:
(S)-2-amino-5-(aminocarbonyl)aminopentanoic acid
(2S)-2-amino-5-(aminocarbonylamino)pentanoic acid
(2S)-2-amino-5-(carbamoylamino)pentanoic acid
L-2-amino-5-ureido-valeric acid
(S)-2-amino-5-ureidopentanoic acid
L(+)-2-amino-5-ureidovaleric acid
alpha-amino-delta-ureidovaleric acid
N5-(aminocarbonyl)-L-Ornithine
N5-(aminocarbonyl)-laevo-Ornithine
N5-carbamoyl-L-ornithine
L-N5-carbamoyl-ornithine
 citrulline
L-citrulline
L-ornithine, N5-(aminocarbonyl)-
delta-ureidonorvaline
 

Articles:

PubMed:L-citrulline Improves Splanchnic Perfusion and Reduces Gut Injury during Exercise.
PubMed:Effects of Watermelon Supplementation on Aortic Hemodynamic Responses to the Cold Pressor Test in Obese Hypertensive Adults.
PubMed:Watermelon juice: potential functional drink for sore muscle relief in athletes.
PubMed:Effects of watermelon supplementation on arterial stiffness and wave reflection amplitude in postmenopausal women.
PubMed:Watermelon extract supplementation reduces ankle blood pressure and carotid augmentation index in obese adults with prehypertension or hypertension.
PubMed:Effects of leucine and citrulline versus non-essential amino acids on muscle protein synthesis in fasted rat: a common activation pathway?
PubMed:The effect of L-citrulline ingestion on ECG QT interval and autonomic nervous system activity.
PubMed:Effects of watermelon supplementation on aortic blood pressure and wave reflection in individuals with prehypertension: a pilot study.
PubMed:A Maillard reaction product enhances eNOS activity in human endothelial cells.
PubMed:Oral L-citrulline supplementation attenuates blood pressure response to cold pressor test in young men.
PubMed:Norfuraneol dephosphorylates eNOS at threonine 495 and enhances eNOS activity in human endothelial cells.
PubMed:Dietary supplementation with watermelon pomace juice enhances arginine availability and ameliorates the metabolic syndrome in Zucker diabetic fatty rats.
PubMed:L-citrulline recycling by argininosuccinate synthetase and lyase in rat gastric fundus.
PubMed:Identification of coumarins from lemon fruit (Citrus limon) as inhibitors of in vitro tumor promotion and superoxide and nitric oxide generation.
PubMed:Spontaneous occurrence of hepatic lipidosis in a group of laboratory cats.
PubMed:Oral administration of arginine and citrulline in the treatment of lysinuric protein intolerance.
PubMed:Formation of N-nitrosoproline by reacting nitrite with L-citrulline and L-arginine.
 
Notes:
Occurs in the juice of watermelon (Citrullus vulgaris) A non-essential amino acid and a precursor of arginine. Citrulline supplements have been claimed to promote energy levels, stimulate the immune system and help detoxify ammonia (a cell toxin). L-citrulline is made from L-ornithine and carbamoyl phosphate in one of the central reactions in the urea cycle. It is also produced from L-arginine as a by-product of the reaction catalyzed by the enzyme NO synthase. L-citrulline, while being an amino acid, is not involved in protein synthesis and is not one of the amino acids coded for by DNA. Although citrulline cannot be incorporated in proteins during protein synthesis, several proteins are known to contain citrulline as an amino acid. These citrulline residues are generated by a family of enzymes called peptidylarginine deiminases (PADs), which convert the amino acid arginine into citrulline. Proteins that contain citrulline residues include myelin basic protein (MBP), fillagrin and several histone proteins.; Citrulline is an amino acid made from ornithine and carbamoyl phosphate in one of the central reactions in the urea cycle. It is also produced from arginine as a by-product of the reaction catalyzed by NOS family (NOS; Citrulline is made from ornithine and carbamoyl phosphate in one of the central reactions in the urea cycle. It is also produced from arginine as a by-product of the reaction catalyzed by NOS family (NOS; EC 1.14.13.39). Arginine is first oxidized into N-hydroxyl-arginine, which is then further oxidized to citrulline concomitant with release of nitric oxide.; EC 1.14.13.39). Citrulline's name is derived from citrullus, the Latin word for watermelon, from which it was first isolated.; EC 1.14.13.39). In this reaction arginine is first oxidized into N-hydroxyl-arginine, which is then further oxidized to citrulline concomitant with the release of nitric oxide.; The organic compound citrulline is an ?-amino acid. Its name is derived from citrullus, the Latin word for watermelon, from which it was first isolated in 1930. It has the idealized formula H2NC(O)NH(CH2)3CH(NH2)CO2H. It is a key intermediate in the urea cycle, the pathway by which mammals excrete ammonia.; The rind of watermelon (Citrullus lanatus) is a good natural source of citrulline.
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