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SML2894

Sigma-Aldrich

HPA-12

≥98% (HPLC)

Synonyme(s) :

(1R,3S)-HPA-12, (1R,3S)-N-(3-Hydroxy-1-hydroxymethyl-3-phenylpropyl)dodecanamide, 16ASC1859, N-[(1R,3S)-3-Hydroxy-1-(hydroxymethyl)-3-phenylpropyl]dodecanamide, N-[(2R,4S)-1,4-Dihydroxy-4-phenylbutan-2-yl]dodecanamide

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About This Item

Formule empirique (notation de Hill):
C22H37NO3
Numéro CAS:
383418-30-2
Poids moléculaire :
363.53
Numéro MDL:
MFCD29472535
Code UNSPSC :
51111800
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 2 mg/mL, clear

Température de stockage

2-8°C

Actions biochimiques/physiologiques

(1R,3S)-HPA-12 is a ceramide (Cer) analog that acts as a Cer transporter (CERT) antagonist and selectively inhibits cellular Cer conversion to sphingomyelin (SM), but not to glucosylceramide, by blocking CERT-mediated Cer ER-to-Golgi transport. Common culture dosing range: 1-10 μM.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Consulter la Bibliothèque de documents

Hannah Scheiblich et al.
Journal of neurochemistry, 143(5), 534-550 (2017-09-25)
Inflammation within the CNS is a major component of many neurodegenerative diseases. A characteristic feature is the generation of microglia-derived factors that play an essential role in the immune response. IL-1β is a pro-inflammatory cytokine released by activated microglia, able
Masaharu Ueno et al.
Organic letters, 15(11), 2869-2871 (2013-05-25)
In response to Berkeš's report revising the stereochemistry of HPA-12, an important ceramide-trafficking inhibitor that was discovered and synthesized and its stereochemistry determined in 2001, the synthesis and the stereochemistry were reinvestigated. A large-scale synthetic method for HPA-12 based on
Andrej Ďuriš et al.
Organic letters, 13(7), 1642-1645 (2011-03-01)
The practical stereodivergent route to both syn- and anti-diastereomers of 1-substituted 3-aminobutane-1,4-diols based on the crystallization-induced asymmetric transformation (CIAT) approach was completed. This led to the revision of the reported stereochemistry of the first inhibitor of CERT-dependent ceramide trafficking HPA-12
S Yasuda et al.
The Journal of biological chemistry, 276(47), 43994-44002 (2001-09-08)
Ceramide produced at the endoplasmic reticulum (ER) is transported to the lumen of the Golgi apparatus for conversion to sphingomyelin (SM). N-(3-Hydroxy-1-hydroxymethyl-3-phenylpropyl)dodecanamide (HPA-12) is a novel analog of ceramide. Metabolic labeling experiments showed that HPA-12 inhibits conversion of ceramide to
Noriyuki Otsuki et al.
Journal of virology, 92(1) (2017-10-27)
Rubella virus (RuV) causes a systemic infection, and transplacental fetal infection causes congenital rubella syndrome. In this study, we showed that treatment of cells with sphingomyelinase inhibited RuV infection. Assays using inhibitors of serine palmitoyl transferase and ceramide transport protein
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