13031-64-6,MFCD00236495
Catalog No.:AA009DXU

13031-64-6 | C2 DIHYDROCERAMIDE

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Purity
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1mg
≥98%
in stock  
$46.00   $32.00
- +
5mg
≥98%
in stock  
$125.00   $87.00
- +
10mg
≥98%
in stock  
$219.00   $153.00
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  • Technical Information
  • Properties
  • Literature
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA009DXU
Chemical Name:
C2 DIHYDROCERAMIDE
CAS Number:
13031-64-6
Molecular Formula:
C20H41NO3
Molecular Weight:
343.5444
MDL Number:
MFCD00236495
SMILES:
CCCCCCCCCCCCCCCC(C(NC(=O)C)CO)O
Properties
Computed Properties
 
Complexity:
284  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
24  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0  
Rotatable Bond Count:
17  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
6.1  

Literature

Title: Cell density-dependent reduction of dihydroceramide desaturase activity in neuroblastoma cells.

Journal: Journal of lipid research 20120501

Title: Analysis of sphingolipids in extracted human plasma using liquid chromatography electrospray ionization tandem mass spectrometry.

Journal: Analytical biochemistry 20120415

Title: Dihydroceramide desaturase and dihydrosphingolipids: debutant players in the sphingolipid arena.

Journal: Progress in lipid research 20120401

Title: Dihydroceramide accumulation and reactive oxygen species are distinct and nonessential events in 4-HPR-mediated leukemia cell death.

Journal: Biochemistry and cell biology = Biochimie et biologie cellulaire 20120401

Title: Gamma-tocotrienol induces apoptosis and autophagy in prostate cancer cells by increasing intracellular dihydrosphingosine and dihydroceramide.

Journal: International journal of cancer 20120201

Title: Myristic acid increases dihydroceramide Δ4-desaturase 1 (DES1) activity in cultured rat hepatocytes.

Journal: Lipids 20120201

Title: Ablation of dihydroceramide desaturase confers resistance to etoposide-induced apoptosis in vitro.

Journal: PloS one 20120101

Title: Phosphorylated dihydroceramides from common human bacteria are recovered in human tissues.

Journal: PloS one 20110101

Title: Mitochondrial dysfunction links ceramide activated HRK expression and cell death.

Journal: PloS one 20110101

Title: Preparation of (13)C-labeled ceramide by acetic acid bacteria and its incorporation in mice.

Journal: Journal of lipid research 20101101

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Alkaline ceramidase 2 (ACER2) and its product dihydrosphingosine mediate the cytotoxicity of N-(4-hydroxyphenyl)retinamide in tumor cells.

Journal: The Journal of biological chemistry 20100917

Title: Porphyromonas gingivalis lipids inhibit osteoblastic differentiation and function.

Journal: Infection and immunity 20100901

Title: Induction of apoptosis by sphingosine, sphinganine, and C(2)-ceramide in human colon cancer cells, but not by C(2)-dihydroceramide.

Journal: Anticancer research 20100701

Title: Dihydroceramide desaturase activity is modulated by oxidative stress.

Journal: The Biochemical journal 20100329

Title: Alkaline ceramidase 3 (ACER3) hydrolyzes unsaturated long-chain ceramides, and its down-regulation inhibits both cell proliferation and apoptosis.

Journal: The Journal of biological chemistry 20100312

Title: Transcript profiling and lipidomic analysis of ceramide subspecies in mouse embryonic stem cells and embryoid bodies.

Journal: Journal of lipid research 20100301

Title: Simultaneous HPLC analysis of ceramide and dihydroceramide in human hairs.

Journal: Archives of pharmacal research 20091201

Title: Dihydroceramide intracellular increase in response to resveratrol treatment mediates autophagy in gastric cancer cells.

Journal: Cancer letters 20090918

Title: Rapid transmembrane diffusion of ceramide and dihydroceramide spin-labelled analogues in the liquid ordered phase.

Journal: Molecular membrane biology 20090401

Title: Ceramide and cerebrosides from the octocoral Sarcophyton ehrenbergi.

Journal: Journal of natural products 20090327

Title: FTY720 inhibits ceramide synthases and up-regulates dihydrosphingosine 1-phosphate formation in human lung endothelial cells.

Journal: The Journal of biological chemistry 20090227

Title: Increased tumour dihydroceramide production after Photofrin-PDT alone and improved tumour response after the combination with the ceramide analogue LCL29. Evidence from mouse squamous cell carcinomas.

Journal: British journal of cancer 20090224

Title: Ceramides: branched alkyl chains in the sphingolipid siblings of diacylglycerol improve biological potency.

Journal: Bioorganic & medicinal chemistry 20090215

Title: Activation of telomerase and cyclooxygenase-2 in PDGF and FGF inhibition of C2-ceramide-induced apoptosis.

Journal: Journal of cellular physiology 20090201

Title: N-Myristoylation targets dihydroceramide Delta4-desaturase 1 to mitochondria: partial involvement in the apoptotic effect of myristic acid.

Journal: Biochimie 20090101

Title: Retinal flavoprotein autofluorescence as a measure of retinal health.

Journal: Transactions of the American Ophthalmological Society 20081201

Title: N-(4-Hydroxyphenyl)retinamide increases dihydroceramide and synergizes with dimethylsphingosine to enhance cancer cell killing.

Journal: Molecular cancer therapeutics 20080901

Title: (Dihydro)ceramide synthase 1 regulated sensitivity to cisplatin is associated with the activation of p38 mitogen-activated protein kinase and is abrogated by sphingosine kinase 1.

Journal: Molecular cancer research : MCR 20070801

Title: Porphyromonas gingivalis dihydroceramides induce apoptosis in endothelial cells.

Journal: Journal of dental research 20070701

Title: Sphingomyelin synthase 1 suppresses ceramide production and apoptosis post-photodamage.

Journal: Biochemical and biophysical research communications 20070622

Title: Solid-phase synthesis of a combinatorial library of dihydroceramide analogues and its activity in human alveolar epithelial cells.

Journal: Bioorganic & medicinal chemistry 20070101

Title: Cannabinoid receptor-mediated apoptosis induced by R(+)-methanandamide and Win55,212-2 is associated with ceramide accumulation and p38 activation in mantle cell lymphoma.

Journal: Molecular pharmacology 20061101

Title: Dihydroceramide:sphinganine C-4-hydroxylation requires Des2 hydroxylase and the membrane form of cytochrome b5.

Journal: The Biochemical journal 20060715

Title: Dihydroceramide hinders ceramide channel formation: Implications on apoptosis.

Journal: Apoptosis : an international journal on programmed cell death 20060501

Title: Porphyromonas gingivalis lipids and diseased dental tissues.

Journal: Oral microbiology and immunology 20060401

Title: The CLN9 protein, a regulator of dihydroceramide synthase.

Journal: The Journal of biological chemistry 20060203

Title: Asymmetric addition of ceramides but not dihydroceramides promotes transbilayer (flip-flop) lipid motion in membranes.

Journal: Biophysical journal 20050101

Title: Reduced levels of the adenomatous polyposis coli (APC) protein are associated with ceramide-induced apoptosis of colon cancer cells.

Journal: Journal of cancer research and clinical oncology 20041201

Title: Structures and biological activity of phosphorylated dihydroceramides of Porphyromonas gingivalis.

Journal: Journal of lipid research 20041201

Title: Ceramide enhances acrosomal exocytosis triggered by calcium and the calcium ionophore A23187 in boar spermatozoa.

Journal: The Journal of reproduction and development 20041201

Title: Ceramide triggers Weibel-Palade body exocytosis.

Journal: Circulation research 20040806

Title: DES2 protein is responsible for phytoceramide biosynthesis in the mouse small intestine.

Journal: The Biochemical journal 20040501

Title: Ceramide is involved in r(+)-methanandamide-induced cyclooxygenase-2 expression in human neuroglioma cells.

Journal: Molecular pharmacology 20031101

Title: Two mammalian longevity assurance gene (LAG1) family members, trh1 and trh4, regulate dihydroceramide synthesis using different fatty acyl-CoA donors.

Journal: The Journal of biological chemistry 20031031

Title: Metabolism of the unnatural anticancer lipid safingol, L-threo-dihydrosphingosine, in cultured cells.

Journal: Journal of lipid research 20030901

Title: Disruption of lipid order by short-chain ceramides correlates with inhibition of phospholipase D and downstream signaling by FcepsilonRI.

Journal: Journal of cell science 20030801

Title: Apoptotic activities of C2-ceramide and C2-dihydroceramide homologues against HL-60 cells.

Journal: Bioorganic & medicinal chemistry 20030703

Title: Elevation of de novo ceramide synthesis in tumor masses and the role of microsomal dihydroceramide synthase.

Journal: International journal of cancer 20030520

Title: Synthesis of non-natural C2-homo-ceramide and its apoptotic activity against HL-60 cells.

Journal: Bioorganic & medicinal chemistry letters 20030224

Title: Ceramide-induced alterations in dopamine transporter function.

Journal: European journal of pharmacology 20030101

Title: Sphingoid bases and ceramide induce apoptosis in HT-29 and HCT-116 human colon cancer cells.

Journal: Experimental biology and medicine (Maywood, N.J.) 20020501

Title: Ceramide-induced inhibition of Akt is mediated through protein kinase Czeta: implications for growth arrest.

Journal: The Journal of biological chemistry 20020201

Title: Substrate specificity of rat brain ceramidase.

Journal: Journal of lipid research 20020101

Title: [Biologically effective sphingolipids devoid of 4-trans-double bond in the sphingoid hydrocarbon chain].

Journal: Bioorganicheskaia khimiia 20020101

Title: Ceramide modulates nicotinic receptor-dependent Ca(2+) signaling in rat chromaffin cells.

Journal: Journal of neuroscience research 20011115

Title: Synthetic phytoceramides induce apoptosis with higher potency than ceramides.

Journal: Molecular pharmacology 20010501

Title: Comparison of the metabolism of L-erythro- and L-threo-sphinganines and ceramides in cultured cells and in subcellular fractions.

Journal: Biochimica et biophysica acta 20010226

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SDS
Tags:13031-64-6 Molecular Formula|13031-64-6 MDL|13031-64-6 SMILES|13031-64-6 C2 DIHYDROCERAMIDE
Catalog No.: AA009DXU
13031-64-6,MFCD00236495
13031-64-6 | C2 DIHYDROCERAMIDE
Pack Size: 1mg
Purity: ≥98%
in stock
$46.00 $32.00
Pack Size: 5mg
Purity: ≥98%
in stock
$125.00 $87.00
Pack Size: 10mg
Purity: ≥98%
in stock
$219.00 $153.00
Quantity
- +
Add to Card
Order Now
bulk Quotation Request
Technical Information
Catalog Number: AA009DXU
Chemical Name: C2 DIHYDROCERAMIDE
CAS Number: 13031-64-6
Molecular Formula: C20H41NO3
Molecular Weight: 343.5444
MDL Number: MFCD00236495
SMILES: CCCCCCCCCCCCCCCC(C(NC(=O)C)CO)O
Properties
Complexity: 284  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 2  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 24  
Hydrogen Bond Acceptor Count: 3  
Hydrogen Bond Donor Count: 3  
Isotope Atom Count: 0  
Rotatable Bond Count: 17  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: 6.1  
Literature fold

Title: Cell density-dependent reduction of dihydroceramide desaturase activity in neuroblastoma cells.

Journal: Journal of lipid research20120501

Title: Analysis of sphingolipids in extracted human plasma using liquid chromatography electrospray ionization tandem mass spectrometry.

Journal: Analytical biochemistry20120415

Title: Dihydroceramide desaturase and dihydrosphingolipids: debutant players in the sphingolipid arena.

Journal: Progress in lipid research20120401

Title: Dihydroceramide accumulation and reactive oxygen species are distinct and nonessential events in 4-HPR-mediated leukemia cell death.

Journal: Biochemistry and cell biology = Biochimie et biologie cellulaire20120401

Title: Gamma-tocotrienol induces apoptosis and autophagy in prostate cancer cells by increasing intracellular dihydrosphingosine and dihydroceramide.

Journal: International journal of cancer20120201

Title: Myristic acid increases dihydroceramide Δ4-desaturase 1 (DES1) activity in cultured rat hepatocytes.

Journal: Lipids20120201

Title: Ablation of dihydroceramide desaturase confers resistance to etoposide-induced apoptosis in vitro.

Journal: PloS one20120101

Title: Phosphorylated dihydroceramides from common human bacteria are recovered in human tissues.

Journal: PloS one20110101

Title: Mitochondrial dysfunction links ceramide activated HRK expression and cell death.

Journal: PloS one20110101

Title: Preparation of (13)C-labeled ceramide by acetic acid bacteria and its incorporation in mice.

Journal: Journal of lipid research20101101

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters20101101

Title: Alkaline ceramidase 2 (ACER2) and its product dihydrosphingosine mediate the cytotoxicity of N-(4-hydroxyphenyl)retinamide in tumor cells.

Journal: The Journal of biological chemistry20100917

Title: Porphyromonas gingivalis lipids inhibit osteoblastic differentiation and function.

Journal: Infection and immunity20100901

Title: Induction of apoptosis by sphingosine, sphinganine, and C(2)-ceramide in human colon cancer cells, but not by C(2)-dihydroceramide.

Journal: Anticancer research20100701

Title: Dihydroceramide desaturase activity is modulated by oxidative stress.

Journal: The Biochemical journal20100329

Title: Alkaline ceramidase 3 (ACER3) hydrolyzes unsaturated long-chain ceramides, and its down-regulation inhibits both cell proliferation and apoptosis.

Journal: The Journal of biological chemistry20100312

Title: Transcript profiling and lipidomic analysis of ceramide subspecies in mouse embryonic stem cells and embryoid bodies.

Journal: Journal of lipid research20100301

Title: Simultaneous HPLC analysis of ceramide and dihydroceramide in human hairs.

Journal: Archives of pharmacal research20091201

Title: Dihydroceramide intracellular increase in response to resveratrol treatment mediates autophagy in gastric cancer cells.

Journal: Cancer letters20090918

Title: Rapid transmembrane diffusion of ceramide and dihydroceramide spin-labelled analogues in the liquid ordered phase.

Journal: Molecular membrane biology20090401

Title: Ceramide and cerebrosides from the octocoral Sarcophyton ehrenbergi.

Journal: Journal of natural products20090327

Title: FTY720 inhibits ceramide synthases and up-regulates dihydrosphingosine 1-phosphate formation in human lung endothelial cells.

Journal: The Journal of biological chemistry20090227

Title: Increased tumour dihydroceramide production after Photofrin-PDT alone and improved tumour response after the combination with the ceramide analogue LCL29. Evidence from mouse squamous cell carcinomas.

Journal: British journal of cancer20090224

Title: Ceramides: branched alkyl chains in the sphingolipid siblings of diacylglycerol improve biological potency.

Journal: Bioorganic & medicinal chemistry20090215

Title: Activation of telomerase and cyclooxygenase-2 in PDGF and FGF inhibition of C2-ceramide-induced apoptosis.

Journal: Journal of cellular physiology20090201

Title: N-Myristoylation targets dihydroceramide Delta4-desaturase 1 to mitochondria: partial involvement in the apoptotic effect of myristic acid.

Journal: Biochimie20090101

Title: Retinal flavoprotein autofluorescence as a measure of retinal health.

Journal: Transactions of the American Ophthalmological Society20081201

Title: N-(4-Hydroxyphenyl)retinamide increases dihydroceramide and synergizes with dimethylsphingosine to enhance cancer cell killing.

Journal: Molecular cancer therapeutics20080901

Title: (Dihydro)ceramide synthase 1 regulated sensitivity to cisplatin is associated with the activation of p38 mitogen-activated protein kinase and is abrogated by sphingosine kinase 1.

Journal: Molecular cancer research : MCR20070801

Title: Porphyromonas gingivalis dihydroceramides induce apoptosis in endothelial cells.

Journal: Journal of dental research20070701

Title: Sphingomyelin synthase 1 suppresses ceramide production and apoptosis post-photodamage.

Journal: Biochemical and biophysical research communications20070622

Title: Solid-phase synthesis of a combinatorial library of dihydroceramide analogues and its activity in human alveolar epithelial cells.

Journal: Bioorganic & medicinal chemistry20070101

Title: Cannabinoid receptor-mediated apoptosis induced by R(+)-methanandamide and Win55,212-2 is associated with ceramide accumulation and p38 activation in mantle cell lymphoma.

Journal: Molecular pharmacology20061101

Title: Dihydroceramide:sphinganine C-4-hydroxylation requires Des2 hydroxylase and the membrane form of cytochrome b5.

Journal: The Biochemical journal20060715

Title: Dihydroceramide hinders ceramide channel formation: Implications on apoptosis.

Journal: Apoptosis : an international journal on programmed cell death20060501

Title: Porphyromonas gingivalis lipids and diseased dental tissues.

Journal: Oral microbiology and immunology20060401

Title: The CLN9 protein, a regulator of dihydroceramide synthase.

Journal: The Journal of biological chemistry20060203

Title: Asymmetric addition of ceramides but not dihydroceramides promotes transbilayer (flip-flop) lipid motion in membranes.

Journal: Biophysical journal20050101

Title: Reduced levels of the adenomatous polyposis coli (APC) protein are associated with ceramide-induced apoptosis of colon cancer cells.

Journal: Journal of cancer research and clinical oncology20041201

Title: Structures and biological activity of phosphorylated dihydroceramides of Porphyromonas gingivalis.

Journal: Journal of lipid research20041201

Title: Ceramide enhances acrosomal exocytosis triggered by calcium and the calcium ionophore A23187 in boar spermatozoa.

Journal: The Journal of reproduction and development20041201

Title: Ceramide triggers Weibel-Palade body exocytosis.

Journal: Circulation research20040806

Title: DES2 protein is responsible for phytoceramide biosynthesis in the mouse small intestine.

Journal: The Biochemical journal20040501

Title: Ceramide is involved in r(+)-methanandamide-induced cyclooxygenase-2 expression in human neuroglioma cells.

Journal: Molecular pharmacology20031101

Title: Two mammalian longevity assurance gene (LAG1) family members, trh1 and trh4, regulate dihydroceramide synthesis using different fatty acyl-CoA donors.

Journal: The Journal of biological chemistry20031031

Title: Metabolism of the unnatural anticancer lipid safingol, L-threo-dihydrosphingosine, in cultured cells.

Journal: Journal of lipid research20030901

Title: Disruption of lipid order by short-chain ceramides correlates with inhibition of phospholipase D and downstream signaling by FcepsilonRI.

Journal: Journal of cell science20030801

Title: Apoptotic activities of C2-ceramide and C2-dihydroceramide homologues against HL-60 cells.

Journal: Bioorganic & medicinal chemistry20030703

Title: Elevation of de novo ceramide synthesis in tumor masses and the role of microsomal dihydroceramide synthase.

Journal: International journal of cancer20030520

Title: Synthesis of non-natural C2-homo-ceramide and its apoptotic activity against HL-60 cells.

Journal: Bioorganic & medicinal chemistry letters20030224

Title: Ceramide-induced alterations in dopamine transporter function.

Journal: European journal of pharmacology20030101

Title: Sphingoid bases and ceramide induce apoptosis in HT-29 and HCT-116 human colon cancer cells.

Journal: Experimental biology and medicine (Maywood, N.J.)20020501

Title: Ceramide-induced inhibition of Akt is mediated through protein kinase Czeta: implications for growth arrest.

Journal: The Journal of biological chemistry20020201

Title: Substrate specificity of rat brain ceramidase.

Journal: Journal of lipid research20020101

Title: [Biologically effective sphingolipids devoid of 4-trans-double bond in the sphingoid hydrocarbon chain].

Journal: Bioorganicheskaia khimiia20020101

Title: Ceramide modulates nicotinic receptor-dependent Ca(2+) signaling in rat chromaffin cells.

Journal: Journal of neuroscience research20011115

Title: Synthetic phytoceramides induce apoptosis with higher potency than ceramides.

Journal: Molecular pharmacology20010501

Title: Comparison of the metabolism of L-erythro- and L-threo-sphinganines and ceramides in cultured cells and in subcellular fractions.

Journal: Biochimica et biophysica acta20010226

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