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
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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The UPR Activator ATF6 Responds to Proteotoxic and Lipotoxic Stress by Distinct Mechanisms
Tam AB, et al.
Developmental Cell, 46(3), 327-343 (2018)
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
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.
Disruption of sphingolipid metabolism augments ceramide-induced autophagy in preeclampsia
Melland-Smith M, et al.
Autophagy, 11(4), 653-669 (2015)
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
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