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3102-57-6

3102-57-6 structure
3102-57-6 structure
  • Name: C2 Ceramide
  • Chemical Name: N-acetylsphingosine
  • CAS Number: 3102-57-6
  • Molecular Formula: C20H39NO3
  • Molecular Weight: 341.529
  • Catalog: Signaling Pathways Apoptosis Apoptosis
  • Create Date: 2018-02-23 08:00:00
  • Modify Date: 2024-01-02 18:52:24
  • C2 Ceramide (Ceramide 2) is the main lipid of the stratum corneum and a protein phosphatase 1 (PP1) activator. C2 Ceramide activates PP2A and ceramide-activated protein phosphatase (CAPP). C2 Ceramide induces cells differentiation and apoptosis, inhibits mitochondrial respiratory chain complex III. C2 Ceramide is also a skin conditioning agent that protects the epidermal barrier from water loss[1][2][3][4][5].

Name N-acetylsphingosine
Synonyms N-Ethanoyl-D-erythro-sphingosine
MFCD00153903
N-ACETYL-D-SPHINGOSINE
D-erythro-N-acetyl-sphingosine
C14 SPHINGOID BASE
C2:0 CERAMIDE
CERAMIDE C2
N-ACETYLSPHINGOSINE
Acetamide, N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-
C2-D-ERYTHRO-CERAMIDE
ACETYL CERAMIDE
N-acetyl-sphing-4-enine
C2-ceramide
Ceramide,N-Acetylsphingosine
TOC Ceramide
N-acetyl-d-erythro-sphingosine
C2 CERAMIDE
N-[(2S,3R,4E)-1,3-Dihydroxy-4-octadecen-2-yl]acetamide
Description C2 Ceramide (Ceramide 2) is the main lipid of the stratum corneum and a protein phosphatase 1 (PP1) activator. C2 Ceramide activates PP2A and ceramide-activated protein phosphatase (CAPP). C2 Ceramide induces cells differentiation and apoptosis, inhibits mitochondrial respiratory chain complex III. C2 Ceramide is also a skin conditioning agent that protects the epidermal barrier from water loss[1][2][3][4][5].
Related Catalog
Target

Protein phosphatase 1[2] PP2A[4] Ceramide-activated protein phosphatase (CAPP)[4] Apoptosis[1] Mitochondrial respiratory chain complex III[1]

In Vitro C2 Ceramide (5 nM-200 µM; 24 hours; primary mouse osteoblasts) treatment (≤500 nM) promots osteoblast viability, whilst concentrations ≥2 µM significantly reduces osteoblast viability in a dose- and time-dependent manner[1]. C2 Ceramide increases cytoplasmic histone-associated DNA fragments by 5.7- and 11.2-fold at 50 µM and 100 µM C2 Ceramide concentrations respectively in osteoblasts. At these higher concentrations, C2 Ceramide is a potent inducer of apoptosis in osteoblasts[1]. C2 Ceramide up-regulates mRNA expression of angiogenic genes in human dental pulp cells (HDPCs) and increases the migration and capillary tube formation of endothelial cells, whereas PP1 small interfering RNA shows opposite effects. Human dental pulp cells (HDPCs) increases levels of bone morphogenetic protein 2, phosphorylation of Smad 1/5/8, and mRNA expression of runt-related transcription factor 2 and osterix[2]. Cell Viability Assay[1] Cell Line: Primary mouse osteoblasts Concentration: 5 nM-200 µM Incubation Time: 24 hours Result: Murine osteoblasts demonstrated a dose-dependent increase in their survival rate when exposed to low concentrations of 5-500 n M. Increasing concentrations of 20-200µM caused a dose-dependent decrease in mitochondrial succinate dehydrogenase activity and osteoblast survival.
In Vivo The PP1 activator C2 Ceramide increases alkaline phosphatase activity, mineralizes nodule formation, and mRNA expression of dentin matrix protein 1 and dentin sialophosphoprotein. In contrast, knockdown by PP1 small interfering RNA inhibits odontoblastic differentiation[2].
References

[1]. P A Hill, et al. Ceramide-induced Cell Death/Survival in Murine Osteoblasts. J Endocrinol. 2010 Aug;206(2):225-33.

[2]. Ji-Youn Kim, et al. Role of Protein Phosphatase 1 in Angiogenesis and Odontoblastic Differentiation of Human Dental Pulp Cells. J Endod. 2017 Mar;43(3):417-424.

[3]. R T Dobrowsky, et al. Ceramide Stimulates a Cytosolic Protein Phosphatase. J Biol Chem. 1992 Mar 15;267(8):5048-51.

[4]. R T Dobrowsky, et al. Ceramide Activates Heterotrimeric Protein Phosphatase 2A. J Biol Chem. 1993 Jul 25;268(21):15523-30.

[5]. Maria Bernadete Riemma Pierre, et al. Influence of ceramide 2 on in vitro skin permeation and retention of 5-ALA and its ester derivatives, for Photodynamic Therapy. Brazilian Journal of Pharmaceutical Sciences. 2009, 45(1), 109-116.

Density 1.0±0.1 g/cm3
Boiling Point 532.4±50.0 °C at 760 mmHg
Melting Point 93-96ºC
Molecular Formula C20H39NO3
Molecular Weight 341.529
Flash Point 275.8±30.1 °C
Exact Mass 341.292999
PSA 69.56000
LogP 5.90
Vapour Pressure 0.0±3.2 mmHg at 25°C
Index of Refraction 1.485
Storage condition -20°C
Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Safety Phrases S22-S24/25
RIDADR NONH for all modes of transport
HS Code 2924199090
HS Code 2924199090
Summary 2924199090. other acyclic amides (including acyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%