Ectoine - ≥97% , CAS No.96702-03-3

CAS: 96702-03-3 Cat. No.: E305040 Molecular Weight: 142.16

GRADE & PURITY ≥97%

Synonyms

THP(B) | SCHEMBL93532 | WQXNXVUDBPYKBA-YFKPBYRVSA-N | (S)-2-Methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid | 4-Pyrimidinecarboxylic acid, 1,4,5,6-tetrahydro-2-methyl-, (+)- | C06231 | UNII-A0Z3NAU9DP | US9138393, Ectoine | 4-Pyrimidinecarboxylicaci

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

Ectoine is a natural cell protectant, an amino acid derivate produced by bacteria living under extremely harsh environmental conditions. Ectoine serves as an osmoregulatory compatible solute, increasing the hydration of the skin surface and stabilizing lipid layers, which is useful in skincare . Ectoine demonstrates a good safety profile for the treatment of allergic rhinitis

Specifications

Synonyms

THP(B) | SCHEMBL93532 | WQXNXVUDBPYKBA-YFKPBYRVSA-N | (S)-2-Methyl-3, 4, 5, 6-tetrahydropyrimidine-4-carboxylic acid | 4-Pyrimidinecarboxylic acid, 1, 4, 5, 6-tetrahydro-2-methyl-, (+)- | C06231 | UNII-A0Z3NAU9DP | US9138393, Ectoine | 4-Pyrimidinecarboxylicaci

Specifications & Purity

≥97%

Storage

Store at 2-8°C, Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥97%

Names and Identifiers

• Pubchem Sid: 488187790
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488187790
• Canonical Smiles: CC1=N[C@@H](CCN1)C(O)=O
• IUPAC Name: (6S)-2-methyl-1,4,5,6-tetrahydropyrimidine-6-carboxylic acid
• InChIKey: WQXNXVUDBPYKBA-YFKPBYRVSA-N
• INCHI: 1S/C6H10N2O2/c1-4-7-3-2-5(8-4)6(9)10/h5H,2-3H2,1H3,(H,7,8)(H,9,10)/t5-/m0/s1
• Isomeric SMILES: CC1=NCC[C@H](N1)C(=O)O
• Molecular Weight: 142.16
• Reaxy-Rn: 7288977
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=7288977&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 Alpha amino acids
              • Level8 L-alpha-amino acids

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives - Alpha amino acids
• Direct Parent: L-alpha-amino acids
• Alternative Parents: Hydropyrimidine carboxylic acids and derivatives Imidolactams Propargyl-type 1,3-dipolar organic compounds Monocarboxylic acids and derivatives Carboxylic acids Carboximidamides Carboxamidines Azacyclic compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: L-alpha-amino acid - Hydropyrimidine carboxylic acid derivative - Hydropyrimidine - 1,4,5,6-tetrahydropyrimidine - Imidolactam - Amidine - Carboxylic acid amidine - Carboxylic acid - Monocarboxylic acid or derivatives - Carboximidamide - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Organoheterocyclic compound - Azacycle - Organonitrogen compound - Organooxygen compound - Carbonyl group - Organic nitrogen compound - Organic oxygen compound - Organic oxide - Organopnictogen compound - Hydrocarbon derivative - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
• External Descriptors: monocarboxylic acid - carboxamidine - 1,4,5,6-tetrahydropyrimidines

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

Discover Target: CYP3A4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Methanol (Sparingly), Water (Slightly)
• Sensitivity: light sensitive;Hygroscopic
• Specific Rotation[α]: 170° (C=1,MeOH)
• Molecular Weight: 142.160 g/mol
• XLogP3: -0.800
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 142.074 Da
• Monoisotopic Mass: 142.074 Da
• Topological Polar Surface Area: 61.700 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 177.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Bingmei Su, Wen Yang, Yi Zhou, Juan Lin.  (2024)  Efficiently manufacturing ectoine via metabolic engineering and protein engineering of L-2,4-diaminobutyrate transaminase.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:38960226] [10.1016/j.ijbiomac.2024.133612]

2. Zheng Lei, Jinyong Wu, Caiwen Lao, Jin Wang, Yanyi Xu, He Li, Lixia Yuan, Xiangsong Chen, Jianming Yao.  (2025)  Multistep Metabolic Engineering of Escherichia coli for High-Level Ectoine Production.  ACS Synthetic Biology,      [PMID:40131136] [10.1021/acssynbio.4c00876]

3. Beibei Lu, Hui Hu, Guangzhen Yang, Ming Pan, Youdi Wang, Jichuan Zhang, Jianglin Zhang, Jiaheng Zhang.  (2024)  Ultrasound-assisted green and efficient extraction of polysaccharides from Chlorella vulgaris using deep eutectic solvents and improving their performance.  NEW JOURNAL OF CHEMISTRY,  48  (10): (4426-4436).  [PMID:] [10.1039/D3NJ05201J]

4. Zheng Lei, Xiangsong Chen, Lixia Yuan, Jinyong Wu, Jianming Yao.  (2025)  Metabolic Control for High-Efficiency Ectoine Synthesis in Engineered Escherichia coli.  ACS Synthetic Biology,      [PMID:40663095] [10.1021/acssynbio.5c00330]