2-Aminooctadecane-1,3-diol
[CAS# 3102-56-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Alcohol
• Name: 2-Aminooctadecane-1,3-diol
• Molecular Formula: C₁₈H₃₉NO₂
• Molecular Weight: 301.51
• CAS Registry Number: 3102-56-5
• EC Number: 608-571-3
• SMILES: CCCCCCCCCCCCCCCC(C(CO)N)O

Properties

• Density: 0.9±0.1 g/cm³ Calc.^*
• Melting point: 70 - 72 ºC (Expl.)
• Boiling point: 446.2±25.0 ºC 760 mmHg (Calc.)^*
• Flash point: 223.7±23.2 ºC (Calc.)^*
• Solubility: methanol : THF : water (6:3:1): >0.5 mg/mL (Expl.)
• Index of refraction: 1.478 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H319
• Precautionary Statements: P264+P265-P280-P305+P351+P338-P337+P317

Discovory and Applicatios

2-Aminooctadecane-1,3-diol is a long-chain aliphatic amino alcohol that belongs to the class of sphingoid bases, which are fundamental structural components of sphingolipids in biological membranes. It is structurally analogous to naturally occurring sphingosine and phytosphingosine, with a saturated C₁₈ backbone bearing amino and hydroxyl functional groups. This compound plays a crucial role in the field of biochemistry and pharmaceutical research, especially in studies related to lipid metabolism, cell signaling, and skin barrier function.

The molecule was first studied in the context of its biological activity in mimicking the structure of endogenous sphingolipids. It was originally discovered during investigations into the metabolic products of ceramide hydrolysis, where it emerged as a potentially bioactive intermediate or synthetic mimic. Structurally, 2-aminooctadecane-1,3-diol contains an amino group at the 2-position and two hydroxyl groups at the 1- and 3-positions along a straight-chain C₁₈ alkyl backbone. This configuration contributes to its amphiphilic nature, making it suitable for incorporation into lipid bilayers and other hydrophobic environments.

In biological systems, sphingoid bases such as 2-aminooctadecane-1,3-diol are involved in key cellular processes. These include apoptosis, proliferation, and differentiation, largely through their conversion into more complex sphingolipids or bioactive derivatives such as ceramides, sphingomyelins, and glycosphingolipids. Synthetic analogs like 2-aminooctadecane-1,3-diol have been used in biochemical studies to probe the function of native sphingolipids and their role in cell signaling pathways, particularly those regulating programmed cell death and response to stress.

The compound has also been explored in dermatological science due to its structural similarity to phytosphingosine, a major constituent of the stratum corneum lipids in human skin. It has been used in cosmetic formulations to improve skin hydration, barrier repair, and antimicrobial defense. Topical preparations containing this compound or its derivatives have been shown to enhance ceramide synthesis in the epidermis, leading to improved moisture retention and resilience against environmental damage. Its amphipathic nature allows it to integrate effectively into lipid membranes, restoring barrier function in compromised skin conditions such as atopic dermatitis and xerosis.

Additionally, 2-aminooctadecane-1,3-diol has found application in medicinal chemistry as a building block for the synthesis of novel bioactive lipids. Its three functional groups provide multiple points for derivatization, enabling the creation of structurally diverse analogs with potential pharmacological activities. For example, modified derivatives have been tested for anticancer, antibacterial, and anti-inflammatory properties. The compound's synthetic accessibility also makes it a useful scaffold in the design of sphingolipid analogs for therapeutic and diagnostic use.

From a synthetic standpoint, 2-aminooctadecane-1,3-diol can be prepared via several routes, including aminohydroxylation of long-chain alkenes or stepwise functionalization of fatty acid derivatives. Its synthesis often involves the protection of functional groups followed by regioselective transformations to introduce the amino and hydroxyl moieties. The availability of stereoisomers adds an additional dimension, as stereochemistry is crucial for biological activity in many lipid-mediated processes. Enantioselective synthesis or separation of stereoisomers is sometimes employed when chirality is required for specific applications.

In conclusion, 2-aminooctadecane-1,3-diol is a versatile and biologically significant compound used across a range of scientific disciplines. Whether as a research tool in lipidomics, a therapeutic agent in dermatology, or a synthetic intermediate in medicinal chemistry, it serves as a model compound for understanding and exploiting the functions of complex sphingolipid systems in health and disease.

References

1956. Chemistry and biology of lipids. XXIII. A new color reaction of sphingosine and dihydrosphingosine. The Tohoku Journal of Experimental Medicine, 64(1).
DOI: 10.1620/tjem.64.63

2023. The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata).
DOI: 10.5281/zenodo.5794106

2024. Serine enrichment in tumors promotes regulatory T cell accumulation through sphinganine-mediated regulation of c-Fos. Science Immunology, 9(94).
DOI: 10.1126/sciimmunol.adg8817