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CS-W001157 4
Total: USD 88.00

5-Hydroxyanthranilic acid

  • CAS No. 394-31-0

  • Cat. No. CS-W002035
  • Purity≥97%
  • MDL No.MFCD00007870

*For research and further manufacturing use only, not for direct human use.

5-Hydroxyanthranilic acid|CS-W002035

Structure of 394-31-0

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General Information

  • CAS No. 394-31-0
  • Cat. No. CS-W002035
  • Purity ≥97%
  • MDL No. MFCD00007870
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₇NO₃
  • Molecular Weight None
  • Synonym(s) None
  • SMILES O=C(O)C1=CC(O)=CC=C1N

Description

cAMP is used for intracellular signal transduction in many different organisms, conveying the cAMP-dependent pathway. Restoration of several morphological characteristics of normal fibroblasts in sarcoma cells when treated with adenosine-3?: 5?-cyclic monophosphate. In the presence of adenosine 3?:5?-cyclic monophosphate, protein kinase I dissociated into two subunits: a subunit binding adenosine 3?:5?-cyclic monophosphate, and a catalytic subunit. Stimulation of calcium uptake in platelet membrane vesicles by adenosine 3?,5?-cyclic monophosphate.

Application

5-Hydroxyanthranilic acid serves as a key building block in the synthesis of biologically relevant heterocycles, including isoquinolines and tetrahydroisoquinolines. Its dual functionality—phenolic hydroxyl and α-amino carboxylic acid—enables diverse transformations under mild conditions, facilitating efficient peptide coupling and cyclization reactions. The compound exhibits good bench stability and is readily purified by recrystallization, making it well-suited for iterative synthetic sequences in medicinal chemistry and natural product synthesis.

Synthesis

  • Route1

    References

    • Karthikeyan; Jagadeesh, Rajenahally V.; Sree Sandhya; Puttaswamy; Nithya; Kumar, S. Senthil; Bhagat Applied Organometallic Chemistry, 2011 , vol. 25, # 1 p. 34 - 46
  • Route2
    • null|null
      340699-08-3
    • ~93%
    • In-stock
      5-Hydroxyanthranilic acid|CS-W002035
      394-31-0

    References

    • Kumar, C. Vinod; Shivananda; Raju, C. Nagu; Jagadeesh Synthetic Communications, 2010 , vol. 40, # 23 p. 3480 - 3487
  • Route3
    • null|null
      107946-58-7
    • ~%
    • In-stock
      5-Hydroxyanthranilic acid|CS-W002035
      394-31-0

    References

    • Ma, Hengchang; Li, Wenfeng; Wang, Jian; Xiao, Guanghai; Gong, Yuan; Qi, Chunxuan; Feng, Yunpeng; Li, Xiufang; Bao, Zhikang; Cao, Wei; Sun, Qiangsheng; Veaceslav, Caraus; Wang, Feng; Lei, Ziqiang Tetrahedron, 2012 , vol. 68, # 39 p. 8358 - 8366

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   83.55
  • LogP   0.6726
  • H_Acceptors   3
  • H_Donors   3
  • Rotatable_Bonds   1

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