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D3314

Sigma-Aldrich

D-erythro-Dihydrosphingosine

≥98%

Synonym(s):

Sphinganine

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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’.

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Karin Thevissen et al.
Bioorganic & medicinal chemistry letters, 18(13), 3728-3730 (2008-06-06)
The minimal fungicidal concentration (MFC) of dihydrosphingosine (DHS), phytosphingosine (PHS), and five short-chain DHS derivatives was determined for Candida albicans and Candida glabrata. In this respect, a C15- and a C17-homologue of DHS showed a 2- to 10-fold decreased MFC
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)
Jorge L Garaicoa et al.
Journal of prosthodontics : official journal of the American College of Prosthodontists, 27(8), 755-762 (2016-11-22)
Several complications may arise in patients wearing complete prosthetic appliances, including denture-associated infections and mucosal stomatitis due to Candida species. This study evaluated the activity of anti-Candida agents in denture adhesive and the cytotoxicities of these preparations for primary human
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