ceramide 2
1-stearoyl-C18-sphingosine
Identification
| Name | ceramide 2 |
| CAS Number | 100403-19-8 |
| EINECS | 309-560-3 |
| FDA UNII | Search |
| Molecular Formula | C36 H71 N O3 |
| Molecular Weight | 565.96647000 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 694.52 °C. @ 760.00 mm Hg (est) |
| Flash Point | 705.00 °F. TCC ( 373.80 °C. ) (est) |
| logP (o/w) | 13.577 (est) |
| Soluble in | water, 1.111e-009 mg/L @ 25 °C (est) |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | hair conditioning |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | cosmetic ingredient for skin and hair conditioning |
| Recommendation for ceramide 2 usage levels up to | not for fragrance use. |
| Recommendation for ceramide 2 flavor usage levels up to | not for flavor use. |
No supplier data available
Potential Uses
Natural Occurrence
Synonyms
(2S,3R,4E)-2-
acylamino-1,3-octadec-4-enediol
(2S,3R,4E)-2-
acylaminooctadec-4-ene-1,3-diol
N-
acylsphingosine
N-((2S,3R,E)-1,3-
dihydroxyoctadec-4-en-2-yl)stearamide
N-[(2S,3R,4E)-1,3-
dihydroxyoctadec-4-en-2-yl]octadecanamide
N-[(E,2S,3R)-1,3-
dihydroxyoctadec-4-en-2-yl]octadecanamide
N-[(1S,2R,3E)-2-
hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-octadecanamide (ceramide 2)
octadecanamide, N-((2S,3R,E)-1,3-dihydroxyoctadec-4-en-2-yl)-
octadecanamide, N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-
octadecanamide, N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-
N-(
octadecanoyl)-sphing-4-enine
1-
stearoyl-C18-sphingosine
N-
stearoyl-D-sphingosine
PubMed:
New ceramide from the aerial part of Tinospora oblongifolia with cytotoxic activities.
PubMed:
Skin lipids from Saudi Arabian birds.
PubMed:
Development of aceclofenac nanovesicular system using biomaterial for transdermal delivery: physical characterization, ex vivo, in vivo, and anti-inflammatory studies.
PubMed:
Development of a new nanovesicle formulation as transdermal carrier: Formulation, physicochemical characterization, permeation studies and anti-inflammatory activity.
PubMed:
Development and characterization of stable nanovesicular carrier for drug delivery.
PubMed:
The effect of a hydrocolloid dressing containing ceramide-2 on split-thickness wounds in a laser-induced erosion model.
PubMed:
Ceramide-2 nanovesicles for effective transdermal delivery: development, characterization and pharmacokinetic evaluation.
PubMed:
Preparation, characterization and permeation studies of a nanovesicular system containing diclofenac for transdermal delivery.
PubMed:
Neurons and oligodendrocytes recycle sphingosine 1-phosphate to ceramide: significance for apoptosis and multiple sclerosis.
PubMed:
Ceramides and cerebrosides from the marine bryozoan Bugula neritina inhabiting South China Sea.
PubMed:
Stratum corneum lipids, skin barrier function and filaggrin mutations in patients with atopic eczema.
PubMed:
Identification of compounds in adlay (Coix lachryma-jobi L. var. ma-yuen Stapf) seed hull extracts that inhibit lipopolysaccharide-induced inflammation in RAW 264.7 macrophages.
PubMed:
Effect of l-menthol on the thermotropic behavior of ceramide 2/cholesterol mixtures as a model for the intercellular lipids in stratum corneum.
PubMed:
Lipid domain morphologies in phosphatidylcholine-ceramide monolayers.
PubMed:
Saturated fatty acid-mediated inflammation and insulin resistance in adipose tissue: mechanisms of action and implications.
PubMed:
Role of ceramides 2 and 5 in the structure of the stratum corneum lipid barrier.
PubMed:
Synthesis and biological activities of glycosphingolipid analogues from marine sponge Aplysinella rhax.
PubMed:
Evaluation of a new pressure ulcer preventive dressing containing ceramide 2 with low frictional outer layer.
PubMed:
The permeability enhancing mechanism of DMSO in ceramide bilayers simulated by molecular dynamics.
PubMed:
Role of ceramide structure and its microenvironment on the conformational order of model stratum corneum lipids mixtures: an approach by FTIR spectroscopy.
PubMed:
Thermotropic behavior of ceramides and their isolation from wool.
PubMed:
Anticancer activity of a ceramide analog containing a disulfide linkage.
PubMed:
A concise synthesis of tetrahydroxy-LCB, alpha-galactosyl ceramide, and 1,4-dideoxy-1,4-imino-L-ribitol via D-allosamines as key building blocks.
PubMed:
Synthesis of a novel ceramide analogue via Tebbe methylenation and evaluation of its antiproliferative activity.
PubMed:
Heterologous desensitization of the sphingosine-1-phosphate receptors by purinoceptor activation in renal mesangial cells.
PubMed:
The human FA2H gene encodes a fatty acid 2-hydroxylase.
PubMed:
Sphingophosphonolipid molecular species from edible mollusks and a jellyfish.
PubMed:
Recapitulation of oral mucosal tissues in long-term organotypic culture.
PubMed:
Isolation and structure of monomethylated GM3-type ganglioside molecular species from the starfish Luidia maculata.
PubMed:
Inhibition of EGF-mediated receptor activity and cell proliferation by HK1-ceramide, a stable analog of the ganglioside GM3-lactone.
PubMed:
N-(4-hydroxyphenyl)retinamide increases ceramide and is cytotoxic to acute lymphoblastic leukemia cell lines, but not to non-malignant lymphocytes.
PubMed:
Apoptosis--new opportunities for novel therapeutics for heart diseases.
PubMed:
Constituents of ophiuroidea. 1. Isolation and structure of three ganglioside molecular species from the brittle star Ophiocoma scolopendrina.
PubMed:
Interleukin 1 upregulates ovarian prostaglandin endoperoxide synthase-2 expression: evidence for prostaglandin-dependent/ceramide-independent transcriptional stimulation and for message stabilization.
PubMed:
Vitamin C stimulates sphingolipid production and markers of barrier formation in submerged human keratinocyte cultures.
PubMed:
Mouse anti-ceramide antiserum: a specific tool for the detection of endogenous ceramide.
PubMed:
Effect of cholesterol on miscibility and phase behavior in binary mixtures with synthetic ceramide 2 and octadecanoic acid. Infrared studies.
PubMed:
Constituents of holothuroidea. 10. Isolation and structure of a biologically active ganglioside molecular species from the sea cucumber Holothuria leucospilota.
PubMed:
Sphingosine derivatives from the seeds of Allium tuberosum.
PubMed:
Effect of phloretin on the percutaneous absorption of lignocaine across human skin.
PubMed:
Fourier transform infrared spectroscopy and differential scanning calorimetry studies of fatty acid homogeneous ceramide 2.
PubMed:
Mitochondrial free calcium levels (Rhod-2 fluorescence) and ultrastructural alterations in neuronally differentiated PC12 cells during ceramide-dependent cell death.
PubMed:
Ceramide 2 (N-acetyl sphingosine) is associated with reduction in Bcl-2 protein levels by Western blotting and with apoptosis in cultured human keratinocytes.
PubMed:
Insights into the molecular organization of lipids in the skin barrier from infrared spectroscopy studies of stratum corneum lipid models.
PubMed:
The polar-lipid composition of the sphingolipid-producing bacterium Flectobacillus major.
PubMed:
Normal ultrastructure, but altered stratum corneum lipid and protein composition in a mouse model for epidermolytic hyperkeratosis.
PubMed:
Stratum corneum lipid composition and structure in cultured skin substitutes is restored to normal after grafting onto athymic mice.
PubMed:
A novel sulfonic-acid analogue of ceramide is the major extractable lipid of the gram-negative marine bacterium Cyclobacterium marinus WH.
PubMed:
Studies on selectin blockers. 4. Structure-function relationships of sulfated sialyl Lewis X hexasaccharide ceramides toward E-, P-, and L-selectin binding.
PubMed:
The effect of a synthetic ceramide-2 on transepidermal water loss after stripping or sodium lauryl sulfate treatment: an in vivo study.
PubMed:
The role of ceramides 1 and 2 in the stratum corneum lipid organisation.
PubMed:
C2-ceramide primes specifically for the superoxide anion production induced by N-formylmethionylleucyl phenylalanine (fMLP) in human neutrophils.
PubMed:
Synthesis of 2-N-oleoylamino-octadecane-1,3-diol: a new ceramide highly effective for the treatment of skin and hair.
PubMed:
Phosphatidylethanolamine: ceramide-ethanolaminephosphotransferase activity in synaptic plasma membrane vesicles. Influence of some cations and phospholipid environment on transferase activity. Further proof of its location.
PubMed:
Age- and sex-dependent change in stratum corneum sphingolipids.
PubMed:
Sphingolipid metabolism in organotypic mouse keratinocyte cultures.
PubMed:
New ganglioside analogs that inhibit influenza virus sialidase.
PubMed:
Characterization and comparison of lipids in different squid nervous tissues.
PubMed:
Lipid metabolism in various regions of squid giant nerve fiber.
PubMed:
Selective recovery of deranged water-holding properties by stratum corneum lipids.
PubMed:
Analysis of phospho- and phosphonosphingolipids by high-performance liquid chromatography.
PubMed:
Temperature-induced changes in the hydroxy and non-hydroxy fatty acid-containing sphingolipids abundant in the surface membrane of Tetrahymena pyriformis NT-1.
PubMed:
Characteristics of phospholipids in microvillar membranes of octopus photoreceptor cells.
PubMed:
Structural components of sphingophosphonolipids from the ciliated protozoan, Tetrahymena pyriformis WH-14.
PubMed:
Biochemical studies of the excitable membrane of Paramecium tetraurelia. II. Phospholipids of ciliary and other membranes.
PubMed:
Neutral glycosphingolipids containing mannose from the bivalve Corbicula sandai.
PubMed:
Identification of molecular species of ceramide 2-N-methyl-aminoethylphosphonates containing normal fatty acids and dihydroxy long chain bases from Turbo cornutus.
PubMed:
Biochemistry of shellfish lipids. IX. Enzymatic hydrolysis of ceramide 2-aminoethylphosphonate and sphingoethanolamine.
PubMed:
Distribution of ceramide 2-aminoethylphosphonate and ceramide aminoethylphosphate (sphingoethanolamine) in some aquatic animals.