Citrulline
Also known as L-citrulline, delta-Ureidonorvaline, Sitrulline
Key facts
What buyers check first
- CAS number
- 372-75-8
- Formula
- C6H13N3O3
- Molar mass
- 175.19 g/mol
- EC number
- 206-759-6
- HS code
- 292419
- Category
- Amino acids and derivatives
What is Citrulline?
Plain description, key identifiers and synonyms
L-citrulline is the L-enantiomer of citrulline. It has a role as a micronutrient, a protective agent, a nutraceutical, an EC 1.14.13.39 (nitric oxide synthase) inhibitor, a mouse metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a human metabolite. It is an enantiomer of a D-citrulline. It is a tautomer of a L-citrulline zwitterion.
Identifiers
Registry numbers, names and line notations, tap to copy
- IUPAC name
- (2S)-2-amino-5-(carbamoylamino)pentanoic acid
- CAS number
- 372-75-8 CAS number cross-checked
- EC number
- 206-759-6
- Molecular formula
- C6H13N3O3
- UNII
- 29VT07BGDA
- MDL number
- MFCD00064397
- INCI name
- CITRULLINE
- InChIKey
- RHGKLRLOHDJJDR-BYPYZUCNSA-N
- InChI
- InChI=1S/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)/t4-/m0/s1
- Canonical SMILES
- NC(=O)NCCCC(N)C(=O)O
- Isomeric SMILES
- C(C[C@@H](C(=O)O)N)CNC(=O)N
Synonyms
- L-citrulline
- delta-Ureidonorvaline
- Sitrulline
- N5-Carbamoyl-L-ornithine
- (S)-2-Amino-5-ureidopentanoic acid
- L-Cytrulline
- N5-(Aminocarbonyl)-L-ornithine
- Citrulline, L-
- N(delta)-Carbamylornithine
- N5-(Aminocarbonyl)ornithine
- L-2-Amino-5-ureidovaleric acid
- N5-carbamoylornithine
- alpha-Amino-delta-ureidovaleric acid
- (2S)-2-amino-5-(carbamoylamino)pentanoic acid
- L-Ornithine, N5-(aminocarbonyl)-
- 2-Amino-5-ureidovaleric acid
- 2-Amino-5-uredovaleric acid
- Ngamma-carbamylornithine
- N(5)-(aminocarbonyl)-L-ornithine
- alpha-amino-gamma-ureidovaleric acid
- (2S)-2-azaniumyl-5-(carbamoylamino)pentanoate
- H-cit-oh
- L(+)-citrulline
- Ornithine, N5-(aminocarbonyl)-
- N~5~-carbamoyl-L-ornithine
Show all 37 synonymsShow fewer synonyms
- d-ureidonorvaline
- (2S)-2-amino-5-(aminocarbonylamino)pentanoic acid
- CIR
- L-citrullin
- L-(+)-Citrulline
- Ornithine, N5-carbamoyl-, L- (8CI)
- N5-carbamylornithine
- A-amino-d-ureidovaleric acid
- Cytrulline
- Ureidonorvaline
- Ureidovalerate
- H-Orn(carbamoyl)-OH, L-Citrulline
Physical and chemical properties
Measured values and descriptors computed from the structure
Physical and chemical properties
Measured values, check the supplier specification for your grade
No measured properties are recorded for this substance yet. Ask suppliers for a technical data sheet.
Values vary by grade. Ask suppliers for the COA or TDS of the batch you buy.
Computed descriptors
Calculated from the structure, useful for screening and formulation
| Molecular weight | 175.19 g/molcalc.Computed value |
|---|---|
| Exact mass | 175.0957 Dacalc.Computed value |
| LogP (octanol/water) | -1.15calc.Computed value |
| Topological polar surface area | 118.4 Ųcalc.Computed value |
| Hydrogen bond donors | 4calc.Computed value |
| Hydrogen bond acceptors | 3calc.Computed value |
| Rotatable bonds | 5calc.Computed value |
| Heavy atoms | 12calc.Computed value |
| Rings | 0calc.Computed value |
| Aromatic rings | 0calc.Computed value |
| Fraction sp3 carbons | 0.67calc.Computed value |
| Formal charge | 0calc.Computed value |
| Stereocentres | 1calc.Computed value |
| Lipinski rule of five | Passes (0 violations)calc.Computed value |
Calculated for screening. Confirm critical figures with the supplier.
Safety and hazards
GHS classification summary, not a safety data sheet
Hazard statements
- H315Causes skin irritation.
- H319Causes serious eye irritation.
Precautionary statements (9)
- P264Wash skin thoroughly after handling.
- P264 + P265Wash skin thoroughly after handling. Do not touch eyes.
- P280Wear protective gloves, protective clothing, eye protection and face protection.
- P302 + P352If on skin: Wash with plenty of water.
- P305 + P351 + P338If in eyes: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
- P321Specific treatment (see supplemental first aid instructions on the label).
- P332 + P317If skin irritation occurs: Get medical help.
- P337 + P317If eye irritation persists: Get medical help.
- P362 + P364Take off contaminated clothing. And wash it before reuse.
GHS classification summary, not a safety data sheet (SDS). Classifications can differ by supplier, grade and concentration. Always check the supplier's SDS.
Full safety data and first aidCitrulline suppliers
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- China, NantongUnclaimed profileCitrullineGrade, purity and minimum order on requestPrice on request
- China, WuhanUnclaimed profileL-CitrullineGrade, purity and minimum order on requestPrice on request
- China, NingboUnclaimed profileL-CitrullineGrade, purity and minimum order on requestPrice on request
- Belgium, AartselaarUnclaimed profileCitrullineGrade, purity and minimum order on requestPrice on request
- China, NingboUnclaimed profileL-CitrullineGrade, purity and minimum order on requestPrice on request
- China, ZhangjiagangUnclaimed profileL-CitrullineGrade, purity and minimum order on requestPrice on request
- China ManufacturerUnclaimed profileL-CitrullineGrade, purity and minimum order on requestPrice on request
- India, Navi Mumbai ManufacturerUnclaimed profilel-citrullineGrade, purity and minimum order on requestPrice on request
- China, Changsha ManufacturerUnclaimed profileL-CitrullineGrade, purity and minimum order on requestPrice on request
- ChinaUnclaimed profileL-CitrullineGrade, purity and minimum order on requestPrice on request
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Where suppliers are based
159 suppliers in 20 countries
- China73
- United States43
- India8
- Germany7
- United Kingdom4
- Spain3
- and 14 more countries
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Citrulline price
Indicative price range per kg from live supplier offers
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Uses and applications
What the substance is used for, by industry and function
Use classes: Cosmetics.
Industries and functions
Cosmetic ingredient, INCI name CITRULLINE(skin conditioning)
Roles
- Daphnia magna metabolite
- Escherichia coli metabolite
- Saccharomyces cerevisiae metabolite
- anti-anaemic agent
- anti-asthmatic agent
- antihypertensive agent
- antineoplastic agent
- cardiovascular drug
- enzyme inhibitor
- eukaryotic metabolite
- food component
- geroprotector
- human metabolite
- hypoglycemic agent
- metabolite
- micronutrient
- mouse metabolite
- nutraceutical
- nutrient
- pharmaceutical
- physiological role
- plant metabolite
- prokaryotic metabolite
- protective agent
Functional uses
- Softener and conditioner
Cosmetic functions
- Skin conditioning
Pharmacology
Citrulline is a non-essential amino acid. In hepatocytes, L-citrulline is synthesized in the urea cycle by the addition of carbon dioxide and ammonia to ornithine. L-citrulline is converted into L-arginine by the enzymes argininosuccinate synthetase and argininosuccinate lyase in the presence of L-aspartate and ATP. Subsequently, L-arginine is converted to nitric oxide by nitric oxide synthase and L-citrulline is regenerated as a by-product.
Regulatory status
Inventories, regulations and trade controls that list this substance
Health and food
- EU cosmetic ingredient inventory
United States
- TSCA inventory (USA)Status: Active in US commerce
HS code and trade data
Customs classification and reported world trade statistics
Global trade
World import and export statistics for the HS code Citrulline is traded under.
Acyclic amides (including acyclic carbamates) and their derivatives, salts thereof, other
- United States17.5%
- Germany8.8%
- India * partner reported6.7%
* Partner reported figures, a lower bound.
The HS code shown for Citrulline is indicative (it was assigned by structure rules). Confirm the classification with your customs broker before shipping.
Frequently asked questions
Quick answers about Citrulline, based on the data on this page
What is Citrulline?
What is the CAS number of Citrulline?
What is the molecular formula and weight of Citrulline?
What is Citrulline used for?
Is Citrulline hazardous?
What is the HS code of Citrulline?
Where can I buy Citrulline?
Where can I buy Citrulline in India?
What is the price of Citrulline?
Guides for buyers
Practical guides that help when you source, ship or handle Citrulline
- Guide, SafetyHow to read a safety data sheet in 10 minutesA section by section method to pull the essentials out of any 16 section SDS: identity, hazards, composition, storage, PPE, properties, transport and emergency measures.Read
- Guide, SafetyGHS pictograms, signal words and hazard statements explainedA practical guide to the nine GHS pictograms, the signal words Danger and Warning, H and P statements, and how to read a chemical label in seconds.Read
- Article, SourcingHow to write an RFQ that gets fast and accurate quotesWhat suppliers need to quote quickly and comparably: exact product identity, quantity and packing, delivery terms, documents, samples and payment, with a ready to use template.Read
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