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D6908

Sigma-Aldrich

DL-erythro-Dihydrosphingosine

≥99%, synthetic

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C18H39NO2
Número de CAS:
3102-56-5
Peso molecular:
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)

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Certificados de análisis (COA)

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

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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
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
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
Avraham Ashkenazi et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 26(11), 4628-4636 (2012-08-09)
Understanding the structural organization of lipids in the cell and viral membranes is essential for elucidating mechanisms of viral fusion that lead to entry of enveloped viruses into their host cells. The HIV lipidome shows a remarkable enrichment in dihydrosphingomyelin
Jesús Enrique Vizcarra-Olvera et al.
Mycopathologia, 174(3), 247-254 (2012-03-08)
This study was conducted to evaluate the possible protector effect of bentonite and zeolite in Bovans chicks fed a diet containing 59 mg kg(-1) of fumonisin B1 (FB1) during 3 weeks. A total of 200 one-day-old male chicks were treated
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