Skip to Content
Merck
All Photos(3)

Documents

D3314

Sigma-Aldrich

D-erythro-Dihydrosphingosine

≥98%

Synonym(s):

Sphinganine

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C18H39NO2
CAS Number:
764-22-7
Molecular Weight:
301.51
MDL number:
MFCD07371371
UNSPSC Code:
12352211
PubChem Substance ID:
24893744
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

200

Assay

≥98%

form

solid

color

white

solubility

DMSO: 25 mg/mL (warm)
ethanol: 25 mg/mL (warm)

lipid type

sphingolipids

storage temp.

−20°C

SMILES string

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

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+/m0/s1

InChI key

OTKJDMGTUTTYMP-ZWKOTPCHSA-N

Application

D-erythro-Dihydrosphingosine has been used:
  • as a standard lipid in quantification assay
  • in kinetics assay
  • to determine serine palmitoyl transferase activity

Biochem/physiol Actions

D-erythro-Dihydrosphingosine is a natural stereoisomer. The levels of dihydrosphingosine (DHS) is increased during unfolded protein response (UPR).
Biosynthetic precursor to sphingosine; inhibits protein kinase C.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Birgitte Lindegaard et al.
PloS one, 13(1), e0186755-e0186755 (2018-01-18)
Interleukin (IL)-18 is involved in regulation of lipid and glucose metabolism. Mice lacking whole-body IL-18 signalling are prone to develop weight gain and insulin resistance, a phenotype which is associated with impaired fat oxidation and ectopic skeletal muscle lipid deposition.
Sarah Bazarganipour et al.
Journal of clinical medicine, 8(7) (2019-07-07)
The factors that contribute to the development of ulcerative colitis (UC), are still not fully identified. Disruption of the colon barrier is one of the first events leading to invasion of bacteria and activation of the immune system. The colon
The UPR Activator ATF6 Responds to Proteotoxic and Lipotoxic Stress by Distinct Mechanisms
Tam AB, et al.
Developmental Cell, 46(3), 327-343 (2018)
Ruzica Jurakic Toncic et al.
International journal of molecular sciences, 21(6) (2020-03-19)
Dysfunctional skin barrier plays a key role in the pathophysiology of atopic dermatitis (AD), a common inflammatory skin disease. Altered composition of ceramides is regarded as a major cause of skin barrier dysfunction, however it is not clear whether these
Jennifer M Fettweis et al.
Nature medicine, 25(6), 1012-1021 (2019-05-31)
The incidence of preterm birth exceeds 10% worldwide. There are significant disparities in the frequency of preterm birth among populations within countries, and women of African ancestry disproportionately bear the burden of risk in the United States. In the present
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service