Embodiments of the present disclosure are related to improved processes for making L-ornithine phenylacetate without using any silver salts or forming any L-ornithine intermediate salts, such as a benzoate salt. The present processes may be used in the commercial scale manufacturing of L-ornithine phenylacetate with high yields and low impurities.

Embodiments of the present disclosure are related to improved processes for making L-ornithine phenylacetate without using any silver salts or forming any L-ornithine intermediate salts, such as a benzoate salt. The present processes may be used in the commercial scale manufacturing of L-ornithine phenylacetate with high yields and low impurities.

1-Aminocyclopropanecarboxylic acid non-hydrate can be obtained by treating 1-aminocyclopropanecarboxylic acid hydrochloride with a tertiary amine in the presence of a C.sub.3-C.sub.4 alcohol and water, keeping the reaction mixture at 50 C. or below, collecting the precipitated crystal of 1-aminocyclopropanecarboxylic acid 0.5 hydrate by filtration, and heating the obtained crystal to 80 to 245 C.

1-Aminocyclopropanecarboxylic acid non-hydrate can be obtained by treating 1-aminocyclopropanecarboxylic acid hydrochloride with a tertiary amine in the presence of a C.sub.3-C.sub.4 alcohol and water, keeping the reaction mixture at 50 C. or below, collecting the precipitated crystal of 1-aminocyclopropanecarboxylic acid 0.5 hydrate by filtration, and heating the obtained crystal to 80 to 245 C.

1-Aminocyclopropanecarboxylic acid non-hydrate can be obtained by treating 1-aminocyclopropanecarboxylic acid hydrochloride with a tertiary amine in the presence of a C.sub.3-C.sub.4 alcohol and water, keeping the reaction mixture at 50 C. or below, collecting the precipitated crystal of 1-aminocyclopropanecarboxylic acid 0.5 hydrate by filtration, and heating the obtained crystal to 80 to 245 C.

Provided herein are novel solid forms of each of four compounds: (1) heptadecan-9-yl 8-((2-hydroxyethyl)amino)octanoate (Compound 1), (2) heptadecan-9-yl 8-((2-hydroxyethyl)(6-oxo-6-(undecyloxy)hexyl)amino)octanoate (Compound 2), (3) heptadecan-9-yl 8-((2-hydroxyethyl)(8-(nonyloxy)-8-oxooctyl)amino)octanoate (Compound 3), and (6Z,9Z,28Z,31Z)-heptatriaconta-6,9,28,31-tetraen-19-yl 4-(dimethylamino)butanoate (MC3), and related compositions and methods.

Provided herein are novel solid forms of each of four compounds: (1) heptadecan-9-yl 8-((2-hydroxyethyl)amino)octanoate (Compound 1), (2) heptadecan-9-yl 8-((2-hydroxyethyl)(6-oxo-6-(undecyloxy)hexyl)amino)octanoate (Compound 2), (3) heptadecan-9-yl 8-((2-hydroxyethyl)(8-(nonyloxy)-8-oxooctyl)amino)octanoate (Compound 3), and (6Z,9Z,28Z,31Z)-heptatriaconta-6,9,28,31-tetraen-19-yl 4-(dimethylamino)butanoate (MC3), and related compositions and methods.

Zwitterionic monomers, carnitine-derived zwitterionic polymers, carnitine ester cationic monomers, carnitine ester cationic polymers, conjugate compositions including a carnitine-derived zwitterionic polymer, and related compositions' and methods are provided which have various uses including as coatings, pharmaceuticals, diagnostics, encapsulation materials, and antifouling materials, among other utilities.

Zwitterionic monomers, carnitine-derived zwitterionic polymers, carnitine ester cationic monomers, carnitine ester cationic polymers, conjugate compositions including a carnitine-derived zwitterionic polymer, and related compositions' and methods are provided which have various uses including as coatings, pharmaceuticals, diagnostics, encapsulation materials, and antifouling materials, among other utilities.

The disclosure features novel lipids and compositions involving the same. Nanoparticle compositions include a novel lipid as well as additional lipids such as phospholipids, structural lipids, and PEG lipids. Nanoparticle compositions further including therapeutic and/or prophylactics such as RNA are useful in the delivery of therapeutic and/or prophylactics to mammalian cells or organs to, for example, regulate polypeptide, protein, or gene expression.