Basic information
- Standard SMILES
CC(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)O- InChIKey
CAHKINHBCWCHCF-JTQLQIEISA-N- Molecular formula
- C11H13NO4
- Average molar mass
- 223.22 g/mol
- Monoisotopic mass
- 223.0844579
Overview
N-acetyl-L-tyrosine is an N-acetyltyrosine in which the chiral centre has L configuration. It has a role as a biomarker, an EC 2.1.1.4 (acetylserotonin O-methyltransferase) inhibitor and a human urinary metabolite. It is a N-acetyltyrosine and a N-acyl-L-tyrosine. It is a conjugate acid of a N-acetyl-L-tyrosinate.
Names & identifiers
- Preferred name
- N-Acetyl-L-tyrosine
- IUPAC
- (2S)-2-acetamido-3-(4-hydroxyphenyl)propanoic acid
- English name
- N-Acetyl-L-tyrosine
- Molecular formula
- C11H13NO4
- Molecular weight
- 223.23
Names & synonyms
N-Acetyl-L-tyrosineN-AcetyltyrosineAcetyl tyrosineL-Tyrosine, N-acetyl-L-Tyrosine, acetyl-DTXSID7046045N-Acetyltyrosine (VAN)UNII-DA8G610ZO5L-N-acetyl-TyrosineTANOGEN HBTYR-EXCELACETYL L-TYROSINE
Show more names
AC-TYR-OHACETYL-L-TYROSINEACETYLTYROSINEN-ACEYL-L-TYROSINEn-acetyl-l-tyrosin-tyrosineN-Acetyl-Thiazolidine-4-carboxylic acid amino acidN-Ac-TyrN-AC-L-TYR
EINECS 208-671-3NSC 10853Tyrosine, N-acetyl-, L-L-TYROSINE, N-ACETYLDTXCID5026045N-ACETYL-L-TYROSINE [USP-RS]N-ACETYLTYROSINE [EP MONOGRAPH](2S)-2-(acetylamino)-3-(4-hydroxyphenyl)propanoic acid
Database identifiers
- CAS
537-55-3- PubChem CID
- 68310
- DTXSID
DTXSID7046045- ChEMBL
CHEMBL65543- ChEBI
CHEBI:21563- UNII
- DA8G610ZO5
- EC Number
- 208-671-3
- Nikkaji
- J62.819K
Properties
Computed structural properties
- XLogP
- -0.2
- Topological polar surface area
- 86.6 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 259
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Cosmetics
Cosmetic ingredients (Acetyl Tyrosine) -> CIR (Cosmetic Ingredient Review)
Tanning
LogP1.320
Solubility297 mg/mL
Boiling Point530.00 to 533.00 °C. @ 760.00 mm Hg
Melting Point
149-152
149 - 152 °C
Physical DescriptionSolid
Collision Cross Section154.5 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
Physicochemical properties
- Melting point
- 149 · 149-152 °C(lit.)
- alpha
- 47.5 · 47.5 º (c=2, water)
- Boiling point
- 364.51 °C · 364.51°C (rough estimate)
- Density
- 1.2446 · 1.2446 (rough estimate)
- refractive index
- 1.496 · 1.4960 (estimate)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- 2 O: · H2O: soluble25mg/mL
- form
- Crystalline
- pka
- 3.15 · 3.15±0.10(Predicted)
- color
- White to Off-White
- Water Solubility
- Soluble in water (25 mg/ml), and ethanol.
- BRN
- 2697172 · 2697172
- Stability
- Stable. Incompatible with strong oxidizing agents.
- Major Application
- pharmaceutical (small molecule)
- Cosmetics Ingredients Functions
- SKIN CONDITIONINGTANNING
- Cosmetic Ingredient Review (CIR)
- N-Acetyl-L-tyrosine (537-55-3)
- InChI
- 1S/C11H13NO4/c1-7(13)12-10(11(15)16)6-8-2-4-9(14)5-3-8/h2-5,10,14H,6H2,1H3,(H,12,13)(H,15,16)/t10-/m0/s1
- InChIKey
- CAHKINHBCWCHCF-JTQLQIEISA-N
- SMILES
- CC(=O)N[C@@H](Cc1ccc(O)cc1)C(O)=O
- LogP
- 1.32 · 1.320
- CAS DataBase Reference
- 537 · 537-55-3(CAS DataBase Reference)
- FDA UNII
- 8 G610ZO5 · DA8G610ZO5
- NIST Chemistry Reference
- N-acetyl-Tyr(537-55-3)
- EPA Substance Registry System
- N-Acetyl-L-tyrosine (537-55-3)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 5 · GHS05
- Signal word
- Danger
- Hazard statements
- 318 · H318
- Precautionary statements
- 280 i-P310a-P280-P305+P351+P338+P310-P305+P351+P338 · P280i-P310a-P280-P305+P351+P338+P310-P305+P351+P338
- Hazard Codes
- Xi
- Risk Statements
- 41 · 41-36/37/38
- Safety Statements
- 26 · 26-39-36
- WGK Germany
- 3 · 3
- F
- 10 · 10
- TSCA
- TSCA listed
- HS Code
- 29242995 · 29242995
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 15.5% (61 of 394) of reports.
Danger
H318 (84.3%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
P264+P265, P280, P305+P354+P338, and P317 (click each P-code to see the statement)
Aggregated GHS information provided per 394 reports by companies from 4 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: L-Tyrosine, N-acetyl-
L-Tyrosine, N-acetyl-: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazard Classes and CategoriesEye Dam. 1 (84.3%)
Toxicology
Toxicity Summary
The panel concluded that the 115 amino acid alkyl amides listed below are safe in the present practices of use and concentration in cosmetics, when formulated to be non-irritating...Acetyl Tyrosine
Safe for use in cosmetics, with qualifications
Safety data
- F
- 10
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29242995
- risk_code
- 41-36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS05
- hazard_code
- Xi
- safety_code
- 26-39-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H318
- Precautionary statements
- P280i-P310a-P280-P305+P351+P338+P310-P305+P351+P338
Chemistry & industry
Pharmacology
PharmacodynamicsN-acetyltyrosine is used as a high solubility precursor to [DB00135] used due to [DB00135]'s poor solubility. It is deacetylated to form [DB00135].
Mechanism of ActionUsed as a source of [DB00135]. See [DB00135] for more information on its role and pharmacology.
Absorption, Distribution and Excretion
N-acetyltyrosine is eliminated in the urine. The extent of urinary elimination versus utilization in the tissues appears to be related to the rapidity of infusion. When infused slowly in standard doses as in the clinical setting, about 35% is excreted unchanged in the urine. When larger doses are infused rapidly, much higher amounts are excreted reaching values up to 56%. In rat studies it was found that of the drug eliminated in the urine about 74% is present as unchanged N-acetyltyrosine and 23% is present as tyrosine.
Cellular LocationsCytoplasm
Uses & manufacturing
UsesCIR ingredient: Acetyl Tyrosine
Use ClassificationCosmetics -> Tanning
General Manufacturing InformationL-Tyrosine, N-acetyl-: ACTIVE
Applications
UsesN-Acetyl-L-tyrosine is involved in catecholamine production. It can be used as a cell culture media component in the commercial biomanufacture of therapeutic recombinant proteins and monoclonal antibodies.
Upstream & downstream products
Upstream raw materials
Suppliers50 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
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北京安司莫森技术有限公司010-82954736 13391601435 · [email protected]
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上海景颜化工科技有限公司13817811078 · [email protected]
Pure Chemistry Scientific Inc.001-857-928-2050 or 1-888-588-9418 · [email protected]
上海泰坦科技股份有限公司400-6009262 15618770481 · [email protected]
上海隆盛化工有限公司58099637 13585536065 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
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武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
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上海倍卓生物科技有限公司021-61119791,13386096464 · [email protected]
北京环宇世纪化学科技有限公司hysj_bj.com
湖北鑫源顺医药化工有限公司13971561712, 13995564702, 027-50664929 · [email protected]
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HBCChem, Inc.+1-510-219-6317 · [email protected]
上海笛柏生物科技有限公司400-008-9730,021-54359730 400-008-9730 · [email protected]
上海石洋化工有限公司021-56795766 · [email protected]
成都零六生物科技有限公司400-1166-196 13458535857 · [email protected]
四川安派博生物科技有限公司028-65294243 18682730901 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
Additional notes
DefinitionChEBI: N-acetyl-L-tyrosine is an N-acetyltyrosine in which the chiral centre has L configuration. It has a role as an EC 2.1.1.4 (acetylserotonin O-methyltransferase) inhibitor, a biomarker and a human urinary metabolite. It is a N-acyl-L-tyrosine and a N-acetyltyrosine. It is a conjugate acid of a N-acetyl-L-tyrosinate.
Related reactions
6 records
Linked notes
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