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D6908

Sigma-Aldrich

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
Beilstein/REAXYS Number:
1724234
MDL number:
MFCD00079141
UNSPSC Code:
12352211
PubChem Substance ID:
24278382

biological source

synthetic

assay

≥99%

form

powder

solubility

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

storage temp.

−20°C

SMILES string

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

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

InChI key

OTKJDMGTUTTYMP-MSOLQXFVSA-N

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Juliana M Figueiredo et al.
Molecular and biochemical parasitology, 182(1-2), 62-74 (2012-01-10)
In this study, we characterized ceramide synthase (CerS) of the protozoan parasite Trypanosoma cruzi at the molecular and functional levels. TcCerS activity was detected initially in a cell-free system using the microsomal fraction of epimastigote forms of T. cruzi, [(3)H]dihydrosphingosine
Yidi Sun et al.
Molecular biology of the cell, 23(12), 2388-2398 (2012-04-27)
Sphingoid intermediates accumulate in response to a variety of stresses, including heat, and trigger cellular responses. However, the mechanism by which stress affects sphingolipid biosynthesis has yet to be identified. Recent studies in yeast suggest that sphingolipid biosynthesis is regulated
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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