N-palmitoyl homocysteine (PHC)

N-palmitoyl homocysteine (ammonium salt), powder

Empirical Formula (Hill Notation):
CAS Number:
Molecular Weight:




pkg of 1 × 25 mg (870320P-25mg)


Avanti Polar Lipids 870320P

shipped in

dry ice

storage temp.


SMILES string


General description

N-palmitoyl homocysteine (PHC) is a pH sensitive head group modified lipid.


N-palmitoyl homocysteine (PHC) has been used in the synthesis of micelle-encapsulated temozolomide (TMZ) and targeted rapamycin micelles (TRaM).

Biochem/physiol Actions

Liposomes containing pH-sensitive molecules facilitate site-specific drug release in response to the change of pH in the surrounding serum. They deliver drugs or gene fragments into the cytoplasm through the endocytotic pathway. Unlike plain liposomes, pH-sensitive liposomes effectively protect drugs and other encapsulated contents such as enzymes, plasmids, proteins and peptides from being potentially degraded at the lysosomal level. They have a wide range of clinical applications such as a carrier of potent drugs for cancer, pulmonary and infectious diseases, a vaccine adjuvant and a vehicle for contrasting agents during imaging. In addition, pH-sensitive liposomes also facilitate the transport of nucleic acids during gene therapy. DOPE liposomes containing PHC deliver their contents at the early endosome.


5 mL Amber Glass Screw Cap Vial (870320P-25mg)


13 - Non Combustible Solids

WGK Germany


Certificate of Analysis

Certificate of Origin

Y Lee et al.
Wiley interdisciplinary reviews. Nanomedicine and nanobiotechnology, 9(5) (2017-02-16)
The ultimate goal of drug delivery is to increase the bioavailability and reduce the toxic side effects of the active pharmaceutical ingredient (API) by releasing them at a specific site of action. In the case of antitumor therapy, association of...
M B Yatvin et al.
Science (New York, N.Y.), 210(4475), 1253-1255 (1980-12-12)
When pH-sensitive molecules are incorporated into liposomes, drugs can be specifically released from these vesicles by a change of pH in the ambient serum. Liposomes containing the pH-sensitive lipid palmitoyl homocysteine (PHC) were constructed so that the greatest pH differential...
D Collins et al.
Biochimica et biophysica acta, 987(1), 47-55 (1989-12-11)
By combining dioleoylphosphatidylethanolamine (DOPE) with oleic acid (OA), palmitoylhomocysteine (PHC) or dipalmitoylsuccinylglycerol (DPSG) we have prepared pH-sensitive liposomes with different acid sensitivities. DOPE/OA liposomes are the most acid sensitive, while DOPE/DPSG liposomes are the least acid sensitive. Incubation of DOPE/OA...
J Connor et al.
The Journal of cell biology, 101(2), 582-589 (1985-08-01)
We previously showed that liposomes composed of dioleoylphosphatidyl-ethanolamine and palmitoyl-homocysteine (8:2) are highly fusion competent when exposed to an acidic environment of pH less than 6.5. (Connor, J., M. B. Yatvin, and L. Huang, 1984, Proc. Natl. Acad. Sci. USA....
J Connor et al.
Proceedings of the National Academy of Sciences of the United States of America, 81(6), 1715-1718 (1984-03-01)
Sonicated unilamellar liposomes containing phosphatidylethanolamine and palmitoylhomocysteine fuse rapidly when the medium pH is lowered from 7 to 5. Liposome fusion was demonstrated by (i) mixing of the liposomal lipids as shown by resonance energy transfer, (ii) gel filtration, and...

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