Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

SML2894

Sigma-Aldrich

HPA-12

≥98% (HPLC)

Synonym(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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C22H37NO3
CAS Number:
383418-30-2
Molecular Weight:
363.53
MDL number:
MFCD29472535
UNSPSC Code:
51111800
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

Biochem/physiol Actions

(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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
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
Cécile L Bandet et al.
Diabetes, 67(7), 1258-1271 (2018-05-16)
One main mechanism of insulin resistance (IR), a key feature of type 2 diabetes, is the accumulation of saturated fatty acids (FAs) in the muscles of obese patients with type 2 diabetes. Understanding the mechanism that underlies lipid-induced IR is
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service