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860654P

Avanti

sphinganine (d17:0)

Avanti Polar Lipids 860654P, powder

Synonym(s):

D-erythro-sphinganine (C17 base)

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About This Item

Empirical Formula (Hill Notation):
C17H37NO2
CAS Number:
32164-02-6
Molecular Weight:
287.48
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 10 mg (860654P-10mg)
pkg of 1 × 5 mg (860654P-5mg)

manufacturer/tradename

Avanti Polar Lipids 860654P

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

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

InChI

1S/C17H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17(20)16(18)15-19/h16-17,19-20H,2-15,18H2,1H3/t16-,17+/m0/s1

InChI key

KFQUQCFJDMSIJF-DLBZAZTESA-N

General description

Sphinganine (d17:0), also referred to as dihydrosphingosine, is devoid of double bond. Decarboxylating condensation of serine with palmitoyl-CoA yield keto intermediate(2-oxosphinganine), which is then reduced by NADPH to form Sphinganine.

Application

Sphinganine (d17:0) has been used in liquid chromatography-mass spectrometry (LC-MS) for the in-situ estimation of dihydrosphingosine utilization in N-(4-hydroxyphenyl)retinamide (4-HPR) resistant leukemia cells. It is suitable for use as an internal standard in metabolomic study.

Biochem/physiol Actions

Sphinganine (SPA) or D-erythro-sphinganine is involved in sphingolipid biosynthesis pathway. It acts as a precursor for ceramide. SPA has an ability to inhibit the activity of protein kinase c. SPA accumulation enables fumonisin B1 to stimulate apoptosis. It also has an ability to block cholesterol transport in Niemann-Pick Type C (NPC) disease.

Packaging

5 mL Amber Glass Screw Cap Vial (860654P-10mg)
5 mL Amber Glass Screw Cap Vial (860654P-5mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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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Lipids
Basic Neurochemistry: Molecular, Cellular and Medical Aspects., 14(5), 833-876 (2011)
Quantification of sphingosine and sphinganine from crude lipid extracts by HPLC electrospray ionization tandem mass spectrometry
Lieser B, et al.
Journal of Lipid Research, 44(11), 2209-2216 (2003)
C F Roff et al.
Developmental neuroscience, 13(4-5), 315-319 (1991-01-01)
Niemann-Pick Type C (NPC) disease is a cholesterol lipidosis resulting from defective postlysosomal cholesterol transport. In normal cells this segment of cholesterol trafficking is inhibited by treatment with either U18666A or imipramine. Other compounds are also capable of blocking postlysosomal
mTORC2 promotes tumorigenesis via lipid synthesis
Guri Y, et al.
Cancer Cell, 32(6), 807-823 (2017)
Evaluation of bioactive sphingolipids in 4-HPR-resistant leukemia cells
Apraiz A, et al.
BMC Cancer, 11(1), 477-477 (2011)
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