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
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.77
biological source
synthetic (organic)
Quality Level
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
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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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