543-38-4
Product Name:
L-Canavanine
Formula:
C5H12N4O3
Synonyms:
L -α-Amino-γ-(guanidinooxy)-n-butyric acid
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CHEMICAL AND PHYSICAL PROPERTIES
| Physical Description | Solid; [Merck Index] Powder; [Sigma-Aldrich MSDS] |
|---|---|
| Color/Form | Crystals from absolute alcohol |
| Melting Point | 184 °C |
| Solubility | Very soluble in water |
| LogP | -3.324 |
| Stability/Shelf Life | Stable under recommended storage conditions. |
| Optical Rotation | Crystals from dilute alcohol, decomposes at 172 °C. Specific optical rotation: +19.4 deg at 17 °C/D (c = 2). Freely soluble in water /Canavanine sulfate/ |
| Collision Cross Section | 133.3 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards] |
| Other Experimental Properties | Crystals from ethanol, MP 180-182 °C. Soluble in water; practically insoluble in alcohol. Forms a monohydrochloride, MP 190 °C /DL-Canavanine/ |
| Chemical Classes | Biological Agents -> Amino Acids and Derivatives |
SAFETY INFORMATION
| Signal word | Warning |
|---|---|
| Pictogram(s) |
 Exclamation Mark Irritant GHS07 |
| Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
COMPUTED DESCRIPTORS
| Molecular Weight | 176.17 g/mol |
|---|---|
| XLogP3 | -4.8 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 5 |
| Exact Mass | 176.09094026 g/mol |
| Monoisotopic Mass | 176.09094026 g/mol |
| Topological Polar Surface Area | 137 Ų |
| Heavy Atom Count | 12 |
| Formal Charge | 0 |
| Complexity | 178 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 1 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
PRODUCT INTRODUCTION
description
L-canavanine is a non-proteinogenic L-alpha-amino acid that is L-homoserine substituted at oxygen with a guanidino (carbamimidamido) group. Although structurally related to L-arginine, it is non-proteinogenic. It has a role as a phytogenic insecticide and a plant metabolite. It is functionally related to a L-homoserine. It is a conjugate base of a L-canavanine(1+). It is a tautomer of a L-canavanine zwitterion.