D3314
D-erythro-Dihydrosphingosine
≥98%
Synonym(s):
Sphinganine
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About This Item
Empirical Formula (Hill Notation):
C18H39NO2
CAS Number:
Molecular Weight:
301.51
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352211
MDL number:
Product Name
D-erythro-Dihydrosphingosine, ≥98%
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
SMILES string
OC[C@@](N)([H])[C@]([H])(O)CCCCCCCCCCCCCCC
InChI key
OTKJDMGTUTTYMP-ZWKOTPCHSA-N
biological source
synthetic (organic)
assay
≥98%
form
solid
color
white
solubility
DMSO: 25 mg/mL (warm)
ethanol: 25 mg/mL (warm)
lipid type
sphingolipids
storage temp.
−20°C
Quality Level
Related Categories
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
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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.
The Lipid Status in Patients with Ulcerative Colitis: Sphingolipids are Disease-Dependent Regulated.
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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