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Merck
CN

D6908

DL-erythro-Dihydrosphingosine

≥99%, synthetic

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C18H39NO2
CAS Number:
3102-56-5
Molecular Weight:
301.51
PubChem Substance ID:
24278382
UNSPSC Code:
12352211
Beilstein/REAXYS Number:
1724234
MDL number:
MFCD00079141

Key Documents

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SMILES string

CCCCCCCCCCCCCCC[C@H](O)[C@H](N)CO

InChI key

OTKJDMGTUTTYMP-MSOLQXFVSA-N

InChI

1S/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+/m1/s1

biological source

synthetic

assay

≥99%

form

powder

solubility

chloroform/methanol (9:1): 20 mg/mL, clear, colorless to slightly yellow

storage temp.

−20°C

Gene Information

human ... PLD1(5337), PLD2(5338), PLD3(23646), PLD4(122618), PLD5(200150), PPP2CA(5515), PPP2CB(5516), PPP2CBP(5517), PPP2R1A(5518), PPP2R1B(5519), PPP2R2A(5520), PPP2R2B(5521), PPP2R2C(5522), PPP2R3A(5523), PRKCA(5578), PRKCB(5579), PRKCD(5580), PRKCE(5581), PRKCG(5582), PRKCH(5583), PRKCI(5584)

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Biochem/physiol Actions

D-Isomer is the biosynthetic precursor of sphingosine; inhibits protein kinase C, phospholipase A2, and phospholipase D.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
058H5180
123H8395
088H5204
038F8429

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C Sakakura et al.
Biochemical and biophysical research communications, 246(3), 827-830 (1998-06-10)
Sphingosine (Sph) is emerging as an intracellular regulator of cellular differentiation and apoptosis (Ohta, et al., Cancer Res., 55, 691-697, 1995). We have recently found that both Sph and its methylated derivative N,N-dimethylsphingosine (DMS) inhibit mitogen-activated protein kinase (MAPK) activity
D D Archibald et al.
Biochimica et biophysica acta, 1166(2-3), 154-162 (1993-02-24)
The natural product D-erythro-sphingosine and synthetic racemic dihydrosphingosines were examined for their abilities to self-assemble into high-axial-ratio microstructures. When precipitated from methanol/water solution, D-erythro-sphingosine formed a viscoelastic gel composed of 50-nm diameter flexible fibers. These are 'cochleate cylinders' composed of
Sang-Hun Song et al.
Scientific reports, 9(1), 9834-9834 (2019-07-10)
Surfactants during routine washing have a tremendous effect on lipid loss from hair. This study aims to understand the loss of lipids from hair upon contact with surfactants and develop a way to prevent the lipid loss. The change in
Emma M Dangerfield et al.
Chembiochem : a European journal of chemical biology, 13(9), 1349-1356 (2012-05-29)
The immunomodulatory glycolipid α-galactosylceramide (α-GalCer) binds to CD1d and exhibits potent activity as a ligand for invariant CD1d-restricted natural killer-like T cells (iNKT cells). Structural analogues of α-GalCer have been synthesised to determine which components are required for CD1d presentation
Emad Benlasher et al.
Avian diseases, 56(1), 120-127 (2012-05-02)
Fumonisins (FBs) are mycotoxins that are found worldwide in maize and maize products. Their main toxic effects have been well characterized in poultry, but differences between species have been demonstrated. Ducks appeared very sensitive to toxicity, whereas turkeys are more
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