structure of Ceramide np

Ceramide np

CAS No.: 100403-19-8
M. Wt: 397.63488
M. Fa: C24H47NO3
InChI Key: ATGQXSBKTQANOH-UWVGARPKSA-N
Appearance: Crystalline Solid

Names and Identifiers of Ceramide np

CAS Number

100403-19-8

EC Number

812-963-1

IUPAC Name

(Z)-N-[(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]octadec-9-enamide

InChI

InChI=1S/C36H71NO4/c1-3-5-7-9-11-13-15-17-18-19-21-23-25-27-29-31-35(40)37-33(32-38)36(41)34(39)30-28-26-24-22-20-16-14-12-10-8-6-4-2/h17-18,33-34,36,38-39,41H,3-16,19-32H2,1-2H3,(H,37,40)/b18-17-/t33-,34+,36-/m0/s1

InChIKey

ATGQXSBKTQANOH-UWVGARPKSA-N

Canonical SMILES

CCCCCCCCCCCCCCC(C(C(CO)NC(=O)CCCCCCCC=CCCCCCCCC)O)O

Isomeric SMILES

CCCCCCCCCCCCCC[C@H]([C@H]([C@H](CO)NC(=O)CCCCCCC/C=C\CCCCCCCC)O)O

Physical and chemical properties of Ceramide np

Molecular Formula

C24H47NO3

Molecular Weight

397.63488

Storage condition

-20°C

Solubility of Ceramide np

Solvent Dissolution Behavior Temperature Effect pH Effect
Ethanol Slightly soluble to soluble (approximately 1–5% w/v), forms a clear solution Increased temperature significantly improves solubility Stable under neutral to weakly alkaline conditions; acidic conditions may promote hydrolysis
Propylene Glycol Soluble, good solubility (>10% w/v) Higher temperature aids dissolution Tolerates a wide pH range; stability decreases under strong acidic or alkaline conditions
Dimethyl Sulfoxide (DMSO) Highly soluble (>20% w/v), excellent solubility Solubility further increases with temperature Good stability, but prolonged exposure to extreme pH may cause degradation
Diethyl Ether Practically insoluble or slightly soluble Solubility slightly increases with temperature Unaffected by common pH changes, but prone to oxidation
Chloroform Soluble, good solubility Solubility increases with temperature Relatively stable toward acids and bases; avoid contact with strong alkalis
Methanol Soluble (approximately 5–10% w/v) Increased temperature promotes dissolution Better in neutral or weakly alkaline environments; may hydrolyze under strongly acidic conditions
Water Practically insoluble (<0.1% w/v), forms emulsion or colloid High temperature slightly improves dispersibility, but not significantly More stable under weakly acidic or neutral conditions; prone to hydrolysis in alkaline conditions
Glycerol Slightly soluble, requires heating to aid dissolution Heating significantly improves solubility Good stability, but may degrade under high temperature and alkaline conditions
N,N-Dimethylformamide (DMF) Soluble (>15% w/v) Solubility increases with temperature Stable under neutral to weakly alkaline conditions; may be unstable under strong acidic conditions

Routine testing items of Ceramide np

Test Item Common Detection Methods Method Overview
Ceramides High-Performance Liquid Chromatography (HPLC) Uses reversed-phase HPLC to separate ceramide species, combined with UV or evaporative light scattering detection for quantitative analysis. Suitable for separation and determination of various ceramide homologs.
Ceramides Ultra-High Performance Liquid Chromatography-Tandem Mass Spectrometry (UHPLC-MS/MS) A high-resolution, highly sensitive method that enables qualitative and quantitative analysis of ceramide molecules via mass spectrometry. Particularly suitable for detecting trace levels of ceramides in complex matrices.
Ceramides Thin-Layer Chromatography (TLC) Used for preliminary separation and identification of ceramides. Simple to operate and low-cost, but has lower sensitivity and resolution. Mostly used for qualitative or semi-quantitative analysis.
Ceramides Gas Chromatography-Mass Spectrometry (GC-MS) Requires derivatization of ceramides prior to analysis. Applicable for volatile or convertible derivatives. Less commonly used due to complex sample preparation and potential structural degradation.
Ceramides Nuclear Magnetic Resonance Spectroscopy (NMR) Provides detailed structural information of ceramide molecules, useful for structural confirmation and purity assessment. However, it requires expensive equipment and has relatively low sensitivity, so it is typically used as a supplementary technique.
Ceramides UV-Visible Spectrophotometry An indirect measurement method, often combined with colorimetric reactions (e.g., sphingolipid-specific staining) to estimate total ceramide content. Simple to perform but lacks specificity.

Key Milestone of Ceramide np

Year Milestone Event Description
1884 First Discovery German chemist Johann Ludwig Wilhelm Thudichum first isolated and named "ceramide" (Ceramide) while studying the lipid components of brain tissue. The name comes from the Latin "cera" (wax) and the Greek "amide" (amide), due to its waxy nature and amide structure.
1920s–1930s Initial Structural Elucidation Scientists gradually confirmed that ceramide consists of a sphingosine backbone linked to a fatty acid via an amide bond, making it a core structural unit of sphingolipids.
1940s–1950s Initial Elucidation of Biosynthetic Pathways Research revealed that ceramide is a central molecule in sphingolipid metabolism, capable of being converted into complex sphingolipids such as sphingomyelin and cerebrosides, playing a key role in cell membrane structure.
1980s Discovery of Signaling Functions Scientists discovered that ceramide is not only a structural lipid but also acts as a second messenger involved in cellular stress, apoptosis, aging, and other signaling pathways, particularly playing a key role in tumor necrosis factor (TNF)-induced and radiation-induced cell death.
1990s Confirmation of Skin Barrier Function Studies confirmed that ceramide is the main component of intercellular lipids in the stratum corneum of the skin (accounting for about 50%), essential for maintaining the integrity of the skin barrier and preventing water loss. Ceramide deficiency is closely related to skin conditions such as atopic dermatitis and psoriasis.
1990s–2000s Rise of Cosmetic Applications Due to its moisturizing and barrier-repairing properties, ceramide has been widely added to skincare products, becoming a key ingredient in high-end moisturizing, anti-sensitive, and repairing products.
2000s–2010s Development of Synthetic and Plant-derived Ceramides To address ethical and stability issues with animal-derived ceramides, scientists developed yeast fermentation, plant extraction (such as rice bran and wheat), and chemically synthesized ceramide analogs (such as Ceramide NP, AP, EOP, etc.), promoting their large-scale application in cosmetics and medicine.
2010s–Present Exploration of Therapeutic Potential Ceramide metabolic abnormalities have been associated with various diseases, including insulin resistance, cardiovascular diseases, neurodegenerative diseases, and cancer. Drugs targeting ceramide synthases (such as CerS) are emerging as potential therapeutic strategies, currently in preclinical or early clinical research stages.
2020s Precision Skincare and Personalized Applications With the development of skin lipidomics, personalized skincare approaches based on individual ceramide profiles are gradually emerging, driving the development of customized skincare products and skin health assessment technologies.

Physical sample testing spectrum (NMR) of Ceramide np

Physical sample testing spectrum (NMR) of Ceramide np