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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

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About This Item

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

Quality Level

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’.

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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
Sophia Koch-Edelmann et al.
Cellular microbiology, 19(10) (2017-05-26)
Chlamydiaceae are bacterial pathogens that cause diverse diseases in humans and animals. Despite their broad host and tissue tropism, all Chlamydia species share an obligate intracellular cycle of development and have evolved sophisticated mechanisms to interact with their eukaryotic host
Élisabeth Roussel et al.
Journal of virology, 92(23) (2018-09-21)
The assembly of new herpes simplex virus 1 (HSV-1) particles takes place in the nucleus. These particles then travel across the two nuclear membranes and acquire a final envelope from a cellular compartment. The contribution of the cell to the
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

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