D-erythro-sphinganine (C20 base) - ≥98% , CAS No.24006-62-0

CAS: 24006-62-0 Cat. No.: D130703 Molecular Weight: 329.561

GRADE & PURITY ≥98%

Synonyms

icosasphinganine | CHEBI:64905 | DTXSID00469532 | icosadihydrosphingosine | Sphinganine (d20:0) | dihydrosphingosine (C20) | Sphinganine (d20:0), D-erythro-sphinganine (C20 base), powder | C20 sphinganine | D-erythro-C20-Dihydrosphingosine | DHS (C20) | e

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Product introduction

Sphinganine (d20:0), also known as C20 dihydrosphingosine or icosasphinganine, is a C20 analog of sphinganine. Sphinganine is a derivative of sphingosine. It is formed in endoplasmic reticulum, by decarboxylating condensation of palmitoyl-CoA and serine.

Application

Sphinganine (d20:0) has been used as a standard in gas chromatography-mass spectrometry (GC-MS) for the quantitative analysis of plant sphingolipid long-chain bases.

Specifications

Synonyms

icosasphinganine | CHEBI:64905 | DTXSID00469532 | icosadihydrosphingosine | Sphinganine (d20:0) | dihydrosphingosine (C20) | Sphinganine (d20:0), D-erythro-sphinganine (C20 base), powder | C20 sphinganine | D-erythro-C20-Dihydrosphingosine | DHS (C20) | e

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Ceramide biosynthesis intermediate. Possible role in heat stress-induced cell cycle arrest. Use sphingolipid-related studies and as internal standard. Sphinganine (d20:0) is implicated in yeast heat stress adaptation. Sphinganine inhibits protein kinase C

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

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

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CCCCCCCCCCCCCCCCCC(C(CO)N)O
• IUPAC Name: (2S,3R)-2-aminoicosane-1,3-diol
• InChIKey: UFMHYBVQZSPWSS-VQTJNVASSA-N
• INCHI: 1S/C20H43NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)19(21)18-22/h19-20,22-23H,2-18,21H2,1H3/t19-,20+/m0/s1
• Isomeric SMILES: CCCCCCCCCCCCCCCCC[C@H]([C@H](CO)N)O
• Molecular Weight: 329.561
• Reaxy-Rn: 6712752
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=6712752&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic nitrogen compounds
    • Class Organonitrogen compounds
      • Subclass Amines
        • Level5 Alkanolamines
          • Level6 1,2-aminoalcohols

• Kingdom: Organic compounds
• Superclass: Organic nitrogen compounds
• Class: Organonitrogen compounds
• Subclass: Amines
• Intermediate Tree Nodes: Alkanolamines
• Direct Parent: 1,2-aminoalcohols
• Alternative Parents: Secondary alcohols Primary alcohols Organopnictogen compounds Monoalkylamines Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Secondary alcohol - 1,2-aminoalcohol - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Primary amine - Primary alcohol - Organooxygen compound - Primary aliphatic amine - Alcohol - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.
• External Descriptors: 2-aminoicosane-1,3-diol

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

Chemical and Physical Properties

• Molecular Weight: 329.600 g/mol
• XLogP3: 6.900
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 18
• Exact Mass: 329.329 Da
• Monoisotopic Mass: 329.329 Da
• Topological Polar Surface Area: 66.500 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 224.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• 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. Jiying Zhu, Wei Jia, Jian Peng.  (2024)  Dissecting the binding effect of Crocetin glucosyltransferase 2 in crocetin biotransformation in saffron (Crocus sativus L.) from different origins.  FOOD CHEMISTRY,      [PMID:38838622] [10.1016/j.foodchem.2024.139917]