DL-erythro-Dihydrosphingosine
- Product Name
- DL-erythro-Dihydrosphingosine
- CAS No.
- 3102-56-5
- Chemical Name
- DL-erythro-Dihydrosphingosine
- Synonyms
- DIHYDROSPHINGOSINE;D-ERYTHRO-SPHINGANINE;D-ERYTHRO-DIHYDROSPHINGOSINE;DL-ERYTHRO-1,3-DIHYDROXY-2-AMINOOCTADECANE;DL-SPHINGANINE;D,L-ERYTHRO-SPHINGANINE;DL-ERYTHRO-DIHYDROSPHINGOSINE;DIHYDROSPHINGOSINE, D-ERYTHRO;D-ERYTHRO-SPHINGOSINE, DIHYDRO-;D-ERTYTHRO-SPHINGANINE, C18 CHAIN
- CBNumber
- CB6139144
- Molecular Formula
- C18H39NO2
- Formula Weight
- 301.51
- MOL File
- 3102-56-5.mol
DL-erythro-Dihydrosphingosine Property
- Melting point:
- 70-72°C
- Boiling point:
- 446.2±25.0 °C(Predicted)
- Density
- 0.927±0.06 g/cm3(Predicted)
- storage temp.
- −20°C
- solubility
- chloroform/methanol (9:1): 20 mg/mL, clear, colorless to faintly yellow
- pka
- 12.57±0.45(Predicted)
- form
- Solid
- color
- white
- Water Solubility
- Soluble in water (partly miscible), chloroform, 100% warm ethanol (25 mg/ml), warm DMSO (25 mg/ml), and methanol.
- InChI
- InChI=1/C18H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h17-18,20-21H,2-16,19H2,1H3/t17-,18+/s3
- InChIKey
- OTKJDMGTUTTYMP-LHIQYTEENA-N
- SMILES
- C(O)[C@@H](N)[C@@H](O)CCCCCCCCCCCCCCC |&1:2,4,r|
- CAS DataBase Reference
- 3102-56-5(CAS DataBase Reference)
Safety
- WGK Germany
- 3
N-Bromosuccinimide Price
- Product number
- J62103
- Product name
- DL-erythro-Dihydrosphingosine
- Packaging
- 50mg
- Price
- $486
- Updated
- 2021/12/16
- Product number
- 24367
- Product name
- DL-erythro/threo Sphinganine (d18:0)
- Purity
- ≥98%
- Packaging
- 25mg
- Price
- $184
- Updated
- 2024/03/01
- Product number
- D151745
- Product name
- DL-erythro-Dihydrosphingosine
- Packaging
- 2.5mg
- Price
- $100
- Updated
- 2021/12/16
- Product number
- 255144
- Product name
- Dihydrosphingosine
- Packaging
- 10mg
- Price
- $418
- Updated
- 2021/12/16
- Product number
- B6434
- Product name
- (2S,3S)-2-aminooctadecane-1,3-diol
- Packaging
- 10mg
- Price
- $223
- Updated
- 2021/12/16
DL-erythro-Dihydrosphingosine Chemical Properties,Usage,Production
Description
DL-erythro Sphinganine (d18:0) is a precursor of ceramide and sphingosine as well as a substrate of sphingosine kinases, which generate sphinganine-1-phosphate . Sphinganine levels increase significantly in response to certain mycotoxins, including fumonisins as well as in some cancers. This product is a mixture of sphinganine (d18:0) , L-erythro sphinganine (d18:0) , D-threo sphinganine (d18:0) , and L-threo sphinganine (d18:0). [Matreya, LLC. Catalog No. 1324]
Chemical Properties
White Powder
Uses
Biosynthetic precursor of sphingosine. Inhibits protein kinase C
Uses
DL-erythro-Dihydrosphingosine is an inhibitor of PKC (protein kinase C). This compound also blocks PLA2 (phospholipases A2) and the D-sphingosine precursor.
Definition
ChEBI: 2-aminooctadecane-1,3-diol is an aminodiol that is octadecane bearing two hydroxy substituents at positions 1 and 3 as well as an amino substituent at position 2. It is a sphingoid and an aminodiol.
Biological Functions
Sphingosine (Sph) is emerging as an intracellular regulator of cellular differentiation and apoptosis. Three stereoisomers,d-erythro-Sph,l-threo-Sph, and dl-erythro-dihydrosphingosine, were tested in the induction of apoptosis and inhibition of MAPK activity in three different kinds of solid tumour cell lines. d-erythro-Sph was strongest in these effects among the three compounds. l-threo-Sphingosine was partly active. On the other hand,dl-erythro-dihydrosphingosine was inactive[1].
Biological Activity
Protein kinase C inhibitor.
storage
-20°C (desiccate)
Purification Methods
Purify it by recrystallisation from pet ether/EtOAc or CHCl3. The (±)-N-dichloroacetyl derivative has m 142-144o (from MeOH). [Shapiro et al. J Am Chem Soc 80 2170 1958, Shapiro & Sheradsky J Org Chem 28 2157 1963.] The D-isomer crystallises from pet ether/Et2O and has m 78.5-79o, [] 28 +6o (CHCl3/MeOH, 10:1). [Grob & Jenny Helv Chim Acta 35 2106 1953, Jenny & Grob Helv Chim Acta 36 1454 1953, Beilstein 4 I 448, 4 II 757, 4 III 854, 4 IV 1887.]
References
[1] Chouhei Sakakura . “Selectivity of Sphingosine-Induced Apoptosis.” Biochemical and biophysical research communications 246 3 (1998): Pages 827-830.
DL-erythro-Dihydrosphingosine Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from DL-erythro-Dihydrosphingosine manufacturers
- Product
- Phytosphingosine 55%/D-erythro-Dihydrosphingosine 20% mixture 3102-56-5
- Price
- US $0.00-0.00/kg
- Min. Order
- 0.10000000149011612kg
- Purity
- 75%
- Supply Ability
- 2000kgs
- Release date
- 2023-12-18
- Product
- DL-erythro-Dihydrosphingosine 3102-56-5
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 20T
- Release date
- 2024-08-11