ceramide 2
1-stearoyl-C18-sphingosine
 
Notes:
None found
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CAS Number: 100403-19-8Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 309-560-3
XlogP3-AA: 13.90 (est)
Molecular Weight: 565.96647000
Formula: C36 H71 N O3
NMR Predictor: Predict (works with chrome or firefox)
Category: cosmetic ingredient for skin and hair conditioning
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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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)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: hair conditioning
skin conditioning
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Suppliers:
Givaudan
Ceramide II / Uniblend™ 2G
Odor: characteristic
Use: Ceramide II is a nature identical molecule. It is based upon the sphinganines group, which has been identified in natural hair lipids. Ceramide II is also one of the lipids that produce the multilamellar layers of the stratum corneum barrier. These lipids contribute to control water permeability and maintain skin condition without being occlusive.
Lipo Chemicals
Ceramide TIC-001
Odor: characteristic
Use: Ceramide 2 is a nature identical sphingolipid. Ceramide 2 plays a key role in the establishment of the stratum corneum barrier function thus preventing transepidermal water loss to enhance skin moisturization.
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Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
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.
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Safety References:
EPI System: View
ClinicalTrials.gov: search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 5283565
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 2
 N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]octadecanamide (ceramide 2)
Chemidplus: 0100403198
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References:
 N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]octadecanamide (ceramide 2)
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 5283565
Pubchem (sid): 135335258
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
HMDB (The Human Metabolome Database): HMDB04950
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 not found in nature
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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
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Articles:
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.
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