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

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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)

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Safety

WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Alfa Aesar

Product number: J62103
Product name: DL-erythro-Dihydrosphingosine
Packaging: 50mg
Price: $486
Updated: 2021/12/16

Cayman Chemical

Product number: 24367
Product name: DL-erythro/threo Sphinganine (d18:0)
Purity: ≥98%
Packaging: 25mg
Price: $184
Updated: 2024/03/01

TRC

Product number: D151745
Product name: DL-erythro-Dihydrosphingosine
Packaging: 2.5mg
Price: $100
Updated: 2021/12/16

Usbiological

Product number: 255144
Product name: Dihydrosphingosine
Packaging: 10mg
Price: $418
Updated: 2021/12/16

ApexBio Technology

Product number: B6434
Product name: (2S,3S)-2-aminooctadecane-1,3-diol
Packaging: 10mg
Price: $223
Updated: 2021/12/16

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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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DL-erythro-Dihydrosphingosine Suppliers

Canada 1 China 36 Europe 2 Germany 2 Switzerland 2 United Kingdom 10 United States 21 USA 1 Global 75

Alfa Chemistry

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View Lastest Price from DL-erythro-Dihydrosphingosine manufacturers

Chongqing Zhihe Biopharmaceutical Co., Ltd.

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

Shaanxi Dideu Medichem Co. Ltd

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

3102-56-5, DL-erythro-DihydrosphingosineRelated Search:

N-(6-[(7-NITRO-2-1,3-BENZOXADIAZOL-4-YL)AMINO]CAPROYL)-PHYTOSPHINGOSINE Phytosphingosine C2 DIHYDROCERAMIDE C14 Dihydroceramide DL-ERYTHRO-DIHYDROSPHINGOSINE C12 NBD-L-THREO-DIHYDROSPHINGOSINE C6 NBD-D-ERYTHRO-DIHYDROSPHINGOSINE C6 NBD-L-THREO-DIHYDROSPHINGOSINE C12 NBD-D-ERYTHRO-DIHYDROSPHINGOSINE D-ERYTHRO-SPHINGOSINE D-erythro-Dihydro-D-sphingosine-1-phosphate C6 DIHYDROCERAMIDE KRN7000 C8 DIHYDROCERAMIDE C6 NBD SAFINGOL C18 Dihydroceramide C4 Dihydroceramide N-[12-[(7-NITRO-2-1,3-BENZOXADIAZOL-4-YL)AMINO]DODECANOYL]-SPHINGANINE

DL-ERYTHRO-1,3-DIHYDROXY-2-AMINOOCTADECANE

DL-ERYTHRO-2-AMINO-1,3-OCTADECANEDIOL

DL-ERYTHRO-DIHYDROSPHINGOSINE

D,L-ERYTHRO-SPHINGANINE

DL-SPHINGANINE

D-ERYTHRO-DIHYDROSPHINGOSINE

D-ERYTHRO-SPHINGANINE

D-ERTYTHRO-SPHINGANINE, C18 CHAIN

D-ERYTHRO-SPHINGOSINE, DIHYDRO-

DIHYDROSPHINGOSINE

DIHYDROSPHINGOSINE, D-ERYTHRO

[R-(R*,S*)]-2-aminooctadecane-1,3-diol

Dihydrosphingosine,Racemic,Synthetic

1,3-Octadecanediol, 2-amino-, (2S,3R)-

(2S,3R)-2-amino-1,3-Octadecanediol

DL-Erythro-DIHYDROSPHINGOSINE Synthetic

DL-erythro-1,3-Dihydroxy-2-aminooctadecane, DL-erythro-2-Amino-1,3-octadecanediol, DL-Sphinganine

DL-erythro/threo Sphinganine (d18:0)

1,3-Octadecanediol, 2-amino-, (2R,3S)-rel-

DL-ERYTHRO-DIHYDROSPHINGOSINE USP/EP/BP

Phytosphingosine 55%/D-erythro-Dihydrosphingosine 20% mixture

3102-56-5

BioChemical

Biochemicals and Reagents

Enzymes, Inhibitors, and Substrates

Enzyme Inhibitors

Enzyme Inhibitors by Enzyme

P to Q

Protein kinase C

Phospholipase A 2

Sphingolipids

Sphingoid bases

Sphinganines

Lipids

Miscellaneous Natural Products

pharmacetical

Protein Kinase Inhibitors and Activators

Protein Kinase