Basic information
- CAS
123-78-4- Standard SMILES
CCCCCCCCCCCCCC=CC(O)C(N)CO- InChIKey
WWUZIQQURGPMPG-UHFFFAOYSA-N- Molecular formula
- C18H37NO2
- Average molar mass
- 299.5 g/mol
- Monoisotopic mass
- 299.28242942
Overview
2-aminooctadec-4-ene-1,3-diol has been reported in Homo sapiens with data available.
Names & identifiers
- Preferred name
- 2-Aminooctadec-4-ene-1,3-diol
- IUPAC
- 2-aminooctadec-4-ene-1,3-diol
- English name
- D-ERYTHRO-SPHINGOSINE
- Molecular formula
- C18H37NO2
- Molecular weight
- 299.49
Names & synonyms
2-Aminooctadec-4-ene-1,3-diolCHEBI:46964RefChem:46516910140-30-44-Octadecene-1,3-diol, 2-amino-D-SphingenineSCHEMBL19399Erythrosphingosine; erythro-C18-Sphingosine; trans-4-SphingenineSCHEMBL3495512SCHEMBL6854143s22102-amino-1,3-dihydroxy-octadec-4-ene
Show more names
SPHINGOSINED-SPHINGOSINESphingosine (d18:1)CEREBROSIDE4-SPHINGENINE(2S,3R,E)-2-aMinooctadec-4-ene-1,3-diolTRANS-D-ERYTHRO-2-AMINO-4-OCTADECENE-1,3-DIOLSphingenineSPHINGOSINE, D-ERYTHRO(2S,3R,4E)-2-amino-4-Octadecene-1,3-diol
NS00076876D-erythro-Sphingosine (1,2-13C2, 99% ; 1,1-D2, 98%)
Database identifiers
- CAS
123-78-4- PubChem CID
- 1104
Properties
Computed structural properties
- XLogP
- 5.3
- Topological polar surface area
- 66.5 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 15
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 231
Physicochemical properties
- Melting point
- 74.2 · 74.2-78.1 °C
- Boiling point
- 440.8 °C · 440.8°C (rough estimate)
- Density
- 0.9758 · 0.9758 (rough estimate)
- refractive index
- 1.5 · 1.5000 (estimate)
- storage temp.
- -20 °C · -20°C
- solubility
- 20 mg/mL, · chloroform: 20 mg/mL, clear, colorless to very faintly yellow
- form
- Powder or Waxy Solid
- pka
- 11.8 · 11.80±0.45(Predicted)
- color
- White to cream
- biological source
- synthetic
- Merck
- 14 · 14,8747
- BRN
- 1727294 · 1727294
- Stability
- Stable. Incompatible with strong acids, strong bases, strong oxidizing agents.
- InChI
- 1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/m0/s1
- InChIKey
- WWUZIQQURGPMPG-KRWOKUGFSA-N
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 3.3% (1 of 30) of reports.
Warning
H315 (96.7%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 30 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (96.7%)
Safety data
- F
- 1-8-10
- wgk
- 3
- hs_code
- 29221985
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Aquatic Chronic 4
- Precautionary statements
- P261-P271-P280
Chemistry & industry
Applications
DescriptionSphingosine (123-78-4) is an inhibitor of protein kinase C (IC50 = 1-3 μM).1 It is abundant in cell membranes and is an important mediator in various biochemical pathways.2-4
UsesSelective inhibitor of protein kinase C activity and phorbol dibutyrate binding in vitro in human platelets; does not inhibit protein kinase A or myosin light chain kinase; inhibits calmodulin-dependent enzymes; natural isomer of sphingosine
UsesD-erythro-Sphingosine is used to inhibits protein kinase C and calmodulin-dependent enzymes, induces apoptosis. And also used to constituent of cell membranes.
UsesSphingosine (d18:1) has been used:for sphingosine inhalations studies in mice to evaluate its therapeutic potential in respiratory epithelial cellsto investigate its effect on Pseudomonas aeruginosa strainsas a standard in liquid chromatography tandem mass spectrophotometry for the quantification of epidermal ceramides
General DescriptionSphingosine (d18:1) is a spingoid base present in plant and animals. It has 2-amino-1,3-diol functionality and its extraction from animal tissue is laborious. Sphingosine (d18:1) synthesis is performed by chirospecific method using D-galactose.
Suppliers100 total
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
宜昌众意泰贸易有限公司0717-6449896 13886658719 · [email protected]
Hangzhou Verychem Science And Technology Co.Ltd+86-86-57188162785 +8613606544505 · [email protected]
江西瑞威尔生物科技有限公司400-880-2824 18107960669 · [email protected]
Related reactions
1 records
Compound notes
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