6754-13-8,MFCD01674580
Catalog No.:AA005MRN

6754-13-8 | Helenalin

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Purity
Availability
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Quantity
  
1mg
≥98%
in stock  
$720.00   $504.00
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  • Technical Information
  • Properties
  • Literature
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA005MRN
Chemical Name:
Helenalin
CAS Number:
6754-13-8
Molecular Formula:
C15H18O4
Molecular Weight:
262.3010
MDL Number:
MFCD01674580
SMILES:
C=C1C(=O)O[C@H]2[C@@H]1[C@H](O)[C@]1(C)C(=O)C=C[C@H]1[C@@H](C2)C
NSC Number:
85236
Properties
Computed Properties
 
Complexity:
506  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
6  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
19  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0  
Rotatable Bond Count:
0  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
1.4  

Literature

Title: Suppressive effects of antimycotics on thymic stromal lymphopoietin production in human keratinocytes.

Journal: Journal of dermatological science 20130901

Title: Helenalin-induced apoptosis is dependent on production of reactive oxygen species and independent of induction of endoplasmic reticulum stress in renal cell carcinoma.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20130301

Title: Enantiomeric derivatives of tokinolide B: absolute configuration and biological properties.

Journal: Journal of natural products 20120525

Title: Supercritical fluid extraction assisted isolation of sesquiterpene lactones with antiproliferative effects from Centipeda minima.

Journal: Phytochemistry 20120401

Title: NF-κB p65 repression by the sesquiterpene lactone, Helenalin, contributes to the induction of autophagy cell death.

Journal: BMC complementary and alternative medicine 20120101

Title: Helenalin bypasses Bcl-2-mediated cell death resistance by inhibiting NF-κB and promoting reactive oxygen species generation.

Journal: Biochemical pharmacology 20110901

Title: Activation and induction of cytosolic phospholipase A2 by TNF-α mediated through Nox2, MAPKs, NF-κB, and p300 in human tracheal smooth muscle cells.

Journal: Journal of cellular physiology 20110801

Title: Quantitative analysis of sesquiterpene lactones in extract of Arnica montana L. by 1H NMR spectroscopy.

Journal: Journal of pharmaceutical and biomedical analysis 20110105

Title: Mycobacterium tuberculosis-infected human monocytes down-regulate microglial MMP-2 secretion in CNS tuberculosis via TNFα, NFκB, p38 and caspase 8 dependent pathways.

Journal: Journal of neuroinflammation 20110101

Title: Surface plasmon resonance analysis of nuclear factor-kappaB protein interactions with the sesquiterpene lactone helenalin.

Journal: Analytical biochemistry 20100601

Title: Discovery and development of natural product-derived chemotherapeutic agents based on a medicinal chemistry approach.

Journal: Journal of natural products 20100326

Title: Dibenzylbutyrolactone lignans from Forsythia koreana fruits attenuate lipopolysaccharide-induced inducible nitric oxide synthetase and cyclooxygenase-2 expressions through activation of nuclear factor-κb and mitogen-activated protein kinase in RAW264.7 cells.

Journal: Biological & pharmaceutical bulletin 20100101

Title: Helenalin suppresses essential immune functions of activated CD4+ T cells by multiple mechanisms.

Journal: Molecular immunology 20090901

Title: Dimethylfumarate inhibits NF-{kappa}B function at multiple levels to limit airway smooth muscle cell cytokine secretion.

Journal: American journal of physiology. Lung cellular and molecular physiology 20090801

Title: Effects of hyaluronan oligosaccharide on the expression of MMP-1 in periodontal ligament cells.

Journal: Archives of oral biology 20090801

Title: Overexpression of HO-1 protects against TNF-alpha-mediated airway inflammation by down-regulation of TNFR1-dependent oxidative stress.

Journal: The American journal of pathology 20090801

Title: Sesquiterpene lactones in Arnica montana: helenalin and dihydrohelenalin chemotypes in Spain.

Journal: Planta medica 20090501

Title: Cigarette smoke extract induces cytosolic phospholipase A2 expression via NADPH oxidase, MAPKs, AP-1, and NF-kappaB in human tracheal smooth muscle cells.

Journal: Free radical biology & medicine 20090401

Title: Helenalin-mediated post-transcriptional regulation of p21(Cip1) inhibits 3T3-L1 preadipocyte proliferation.

Journal: Journal of cellular biochemistry 20081015

Title: Use of self-organizing maps and molecular descriptors to predict the cytotoxic activity of sesquiterpene lactones.

Journal: European journal of medicinal chemistry 20081001

Title: Natural sesquiterpene lactones are active against Leishmania mexicana.

Journal: The Journal of parasitology 20081001

Title: Inhibition of Nod2 signaling and target gene expression by curcumin.

Journal: Molecular pharmacology 20080701

Title: Neural networks as valuable tools to differentiate between sesquiterpene lactones' inhibitory activity on serotonin release and on NF-kappaB.

Journal: Journal of medicinal chemistry 20080313

Title: Effect of vehicles on topical application of aloe vera and arnica montana components.

Journal: Drug delivery 20071001

Title: The effect of 17beta-estradiol on IL-6 secretion and NF-kappaB DNA-binding activity in human retinal pigment epithelial cells.

Journal: Immunology letters 20070615

Title: Withaferin a strongly elicits IkappaB kinase beta hyperphosphorylation concomitant with potent inhibition of its kinase activity.

Journal: The Journal of biological chemistry 20070216

Title: The autocrine TNFalpha signalling loop in keratinocytes requires atypical PKC species and NF-kappaB activation but is independent of cholesterol-enriched membrane microdomains.

Journal: Biochemical pharmacology 20070215

Title: Helenalin reduces Staphylococcus aureus infection in vitro and in vivo.

Journal: Veterinary microbiology 20070131

Title: Skin penetration behaviour of sesquiterpene lactones from different Arnica preparations using a validated GC-MSD method.

Journal: Journal of pharmaceutical and biomedical analysis 20070104

Title: Sesquiterpene lactone helenalin suppresses Leydig and adrenocortical cell steroidogenesis by inhibiting expression of the steroidogenic acute regulatory protein.

Journal: Reproductive toxicology (Elmsford, N.Y.) 20061101

Title: Novel effect of helenalin on Akt signaling and Skp2 expression in 3T3-L1 preadipocytes.

Journal: Biochemical and biophysical research communications 20060721

Title: Inhibition of homodimerization of Toll-like receptor 4 by curcumin.

Journal: Biochemical pharmacology 20060628

Title: BLIMP-1 is a target of cellular stress and downstream of the unfolded protein response.

Journal: European journal of immunology 20060601

Title: Development and stability of semisolid preparations based on a supercritical CO2 Arnica extract.

Journal: Journal of pharmaceutical and biomedical analysis 20060503

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Nuclear factor-kappaB p65 and upregulation of interleukin-6 in retinal ischemia/reperfusion injury in rats.

Journal: Brain research 20060407

Title: Development of a structural model for NF-kappaB inhibition of sesquiterpene lactones using self-organizing neural networks.

Journal: Journal of medicinal chemistry 20060406

Title: Transcriptional regulation of VCAM-1 expression by tumor necrosis factor-alpha in human tracheal smooth muscle cells: involvement of MAPKs, NF-kappaB, p300, and histone acetylation.

Journal: Journal of cellular physiology 20060401

Title: TNF-alpha-induced optic nerve degeneration and nuclear factor-kappaB p65.

Journal: Investigative ophthalmology & visual science 20060401

Title: Delayed radioprotection by nuclear transcription factor kappaB -mediated induction of manganese superoxide dismutase in human microvascular endothelial cells after exposure to the free radical scavenger WR1065.

Journal: Free radical biology & medicine 20060315

Title: Involvement of Nrf2, p38, B-Raf, and nuclear factor-kappaB, but not phosphatidylinositol 3-kinase, in induction of hemeoxygenase-1 by dietary polyphenols.

Journal: Molecular pharmacology 20060301

Title: NOD2/CARD15 mediates induction of the antimicrobial peptide human beta-defensin-2.

Journal: The Journal of biological chemistry 20060127

Title: BK-induced cytosolic phospholipase A2 expression via sequential PKC-delta, p42/p44 MAPK, and NF-kappaB activation in rat brain astrocytes.

Journal: Journal of cellular physiology 20060101

Title: Synthesis and anti-viral activity of a series of sesquiterpene lactones and analogues in the subgenomic HCV replicon system.

Journal: Bioorganic & medicinal chemistry 20060101

Title: Potent inhibition of human telomerase by helenalin.

Journal: Cancer letters 20050928

Title: Polysaccharide purified from Ganoderma lucidum induced activation and maturation of human monocyte-derived dendritic cells by the NF-kappaB and p38 mitogen-activated protein kinase pathways.

Journal: Journal of leukocyte biology 20050801

Title: Activation of nuclear factor-kappaB contributes to induction of death receptors and apoptosis by the synthetic retinoid CD437 in DU145 human prostate cancer cells.

Journal: Cancer research 20050715

Title: Apoptosis induction by a novel retinoid-related molecule requires nuclear factor-kappaB activation.

Journal: Cancer research 20050601

Title: Induction of human leukemia HL-60 cell differentiation via a PKC/ERK pathway by helenalin, a pseudoguainolide sesquiterpene lactone.

Journal: European journal of pharmacology 20050328

Title: Involvement of p42/p44 MAPK, JNK, and NF-kappaB in IL-1beta-induced ICAM-1 expression in human pulmonary epithelial cells.

Journal: Journal of cellular physiology 20050201

Title: The trypanocidal effect of sesquiterpene lactones helenalin and mexicanin on cultured epimastigotes.

Journal: The Journal of parasitology 20050201

Title: Intracellular signalings underlying bradykinin-induced matrix metalloproteinase-9 expression in rat brain astrocyte-1.

Journal: Cellular signalling 20041001

Title: New chromanone acids with antibacterial activity from Calophyllum brasiliense.

Journal: Journal of natural products 20040401

Title: Pseudoguaianolide sesquiterpene lactones with high activities against the human malaria parasite Plasmodium falciparum.

Journal: Phytotherapy research : PTR 20040201

Title: Influence of helenanolide-type sesquiterpene lactones on gene transcription profiles in Jurkat T cells and human peripheral blood cells: anti-inflammatory and cytotoxic effects.

Journal: Biochemical pharmacology 20031201

Title: Regulation of microglial inflammatory response by histone deacetylase inhibitors.

Journal: Journal of neurochemistry 20031001

Title: Characterization of the molecular events following impairment of NF-kappaB-driven transcription in neurons.

Journal: Brain research. Molecular brain research 20021230

Title: Anti-trypanosomal activity of helenalin and some structurally related sesquiterpene lactones.

Journal: Planta medica 20020801

Title: Inhibitory effects of helenalin and related compounds on 5-lipoxygenase and leukotriene C(4) synthase in human blood cells.

Journal: Biochemical pharmacology 20011001

Title: Helenalin triggers a CD95 death receptor-independent apoptosis that is not affected by overexpression of Bcl-x(L) or Bcl-2.

Journal: Cancer research 20010801

Title: The influence of glutathione and cysteine levels on the cytotoxicity of helenanolide type sesquiterpene lactones against KB cells.

Journal: Bioorganic & medicinal chemistry 20010801

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SDS
Tags:6754-13-8 Molecular Formula|6754-13-8 MDL|6754-13-8 SMILES|6754-13-8 Helenalin
Catalog No.: AA005MRN
6754-13-8,MFCD01674580
6754-13-8 | Helenalin
Pack Size: 1mg
Purity: ≥98%
in stock
$720.00 $504.00
Quantity
- +
Add to Card
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bulk Quotation Request
Technical Information
Catalog Number: AA005MRN
Chemical Name: Helenalin
CAS Number: 6754-13-8
Molecular Formula: C15H18O4
Molecular Weight: 262.3010
MDL Number: MFCD01674580
SMILES: C=C1C(=O)O[C@H]2[C@@H]1[C@H](O)[C@]1(C)C(=O)C=C[C@H]1[C@@H](C2)C
NSC Number: 85236
Properties
Complexity: 506  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 6  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 19  
Hydrogen Bond Acceptor Count: 4  
Hydrogen Bond Donor Count: 1  
Isotope Atom Count: 0  
Rotatable Bond Count: 0  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: 1.4  
Literature fold

Title: Suppressive effects of antimycotics on thymic stromal lymphopoietin production in human keratinocytes.

Journal: Journal of dermatological science20130901

Title: Helenalin-induced apoptosis is dependent on production of reactive oxygen species and independent of induction of endoplasmic reticulum stress in renal cell carcinoma.

Journal: Toxicology in vitro : an international journal published in association with BIBRA20130301

Title: Enantiomeric derivatives of tokinolide B: absolute configuration and biological properties.

Journal: Journal of natural products20120525

Title: Supercritical fluid extraction assisted isolation of sesquiterpene lactones with antiproliferative effects from Centipeda minima.

Journal: Phytochemistry20120401

Title: NF-κB p65 repression by the sesquiterpene lactone, Helenalin, contributes to the induction of autophagy cell death.

Journal: BMC complementary and alternative medicine20120101

Title: Helenalin bypasses Bcl-2-mediated cell death resistance by inhibiting NF-κB and promoting reactive oxygen species generation.

Journal: Biochemical pharmacology20110901

Title: Activation and induction of cytosolic phospholipase A2 by TNF-α mediated through Nox2, MAPKs, NF-κB, and p300 in human tracheal smooth muscle cells.

Journal: Journal of cellular physiology20110801

Title: Quantitative analysis of sesquiterpene lactones in extract of Arnica montana L. by 1H NMR spectroscopy.

Journal: Journal of pharmaceutical and biomedical analysis20110105

Title: Mycobacterium tuberculosis-infected human monocytes down-regulate microglial MMP-2 secretion in CNS tuberculosis via TNFα, NFκB, p38 and caspase 8 dependent pathways.

Journal: Journal of neuroinflammation20110101

Title: Surface plasmon resonance analysis of nuclear factor-kappaB protein interactions with the sesquiterpene lactone helenalin.

Journal: Analytical biochemistry20100601

Title: Discovery and development of natural product-derived chemotherapeutic agents based on a medicinal chemistry approach.

Journal: Journal of natural products20100326

Title: Dibenzylbutyrolactone lignans from Forsythia koreana fruits attenuate lipopolysaccharide-induced inducible nitric oxide synthetase and cyclooxygenase-2 expressions through activation of nuclear factor-κb and mitogen-activated protein kinase in RAW264.7 cells.

Journal: Biological & pharmaceutical bulletin20100101

Title: Helenalin suppresses essential immune functions of activated CD4+ T cells by multiple mechanisms.

Journal: Molecular immunology20090901

Title: Dimethylfumarate inhibits NF-{kappa}B function at multiple levels to limit airway smooth muscle cell cytokine secretion.

Journal: American journal of physiology. Lung cellular and molecular physiology20090801

Title: Effects of hyaluronan oligosaccharide on the expression of MMP-1 in periodontal ligament cells.

Journal: Archives of oral biology20090801

Title: Overexpression of HO-1 protects against TNF-alpha-mediated airway inflammation by down-regulation of TNFR1-dependent oxidative stress.

Journal: The American journal of pathology20090801

Title: Sesquiterpene lactones in Arnica montana: helenalin and dihydrohelenalin chemotypes in Spain.

Journal: Planta medica20090501

Title: Cigarette smoke extract induces cytosolic phospholipase A2 expression via NADPH oxidase, MAPKs, AP-1, and NF-kappaB in human tracheal smooth muscle cells.

Journal: Free radical biology & medicine20090401

Title: Helenalin-mediated post-transcriptional regulation of p21(Cip1) inhibits 3T3-L1 preadipocyte proliferation.

Journal: Journal of cellular biochemistry20081015

Title: Use of self-organizing maps and molecular descriptors to predict the cytotoxic activity of sesquiterpene lactones.

Journal: European journal of medicinal chemistry20081001

Title: Natural sesquiterpene lactones are active against Leishmania mexicana.

Journal: The Journal of parasitology20081001

Title: Inhibition of Nod2 signaling and target gene expression by curcumin.

Journal: Molecular pharmacology20080701

Title: Neural networks as valuable tools to differentiate between sesquiterpene lactones' inhibitory activity on serotonin release and on NF-kappaB.

Journal: Journal of medicinal chemistry20080313

Title: Effect of vehicles on topical application of aloe vera and arnica montana components.

Journal: Drug delivery20071001

Title: The effect of 17beta-estradiol on IL-6 secretion and NF-kappaB DNA-binding activity in human retinal pigment epithelial cells.

Journal: Immunology letters20070615

Title: Withaferin a strongly elicits IkappaB kinase beta hyperphosphorylation concomitant with potent inhibition of its kinase activity.

Journal: The Journal of biological chemistry20070216

Title: The autocrine TNFalpha signalling loop in keratinocytes requires atypical PKC species and NF-kappaB activation but is independent of cholesterol-enriched membrane microdomains.

Journal: Biochemical pharmacology20070215

Title: Helenalin reduces Staphylococcus aureus infection in vitro and in vivo.

Journal: Veterinary microbiology20070131

Title: Skin penetration behaviour of sesquiterpene lactones from different Arnica preparations using a validated GC-MSD method.

Journal: Journal of pharmaceutical and biomedical analysis20070104

Title: Sesquiterpene lactone helenalin suppresses Leydig and adrenocortical cell steroidogenesis by inhibiting expression of the steroidogenic acute regulatory protein.

Journal: Reproductive toxicology (Elmsford, N.Y.)20061101

Title: Novel effect of helenalin on Akt signaling and Skp2 expression in 3T3-L1 preadipocytes.

Journal: Biochemical and biophysical research communications20060721

Title: Inhibition of homodimerization of Toll-like receptor 4 by curcumin.

Journal: Biochemical pharmacology20060628

Title: BLIMP-1 is a target of cellular stress and downstream of the unfolded protein response.

Journal: European journal of immunology20060601

Title: Development and stability of semisolid preparations based on a supercritical CO2 Arnica extract.

Journal: Journal of pharmaceutical and biomedical analysis20060503

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology20060501

Title: Nuclear factor-kappaB p65 and upregulation of interleukin-6 in retinal ischemia/reperfusion injury in rats.

Journal: Brain research20060407

Title: Development of a structural model for NF-kappaB inhibition of sesquiterpene lactones using self-organizing neural networks.

Journal: Journal of medicinal chemistry20060406

Title: Transcriptional regulation of VCAM-1 expression by tumor necrosis factor-alpha in human tracheal smooth muscle cells: involvement of MAPKs, NF-kappaB, p300, and histone acetylation.

Journal: Journal of cellular physiology20060401

Title: TNF-alpha-induced optic nerve degeneration and nuclear factor-kappaB p65.

Journal: Investigative ophthalmology & visual science20060401

Title: Delayed radioprotection by nuclear transcription factor kappaB -mediated induction of manganese superoxide dismutase in human microvascular endothelial cells after exposure to the free radical scavenger WR1065.

Journal: Free radical biology & medicine20060315

Title: Involvement of Nrf2, p38, B-Raf, and nuclear factor-kappaB, but not phosphatidylinositol 3-kinase, in induction of hemeoxygenase-1 by dietary polyphenols.

Journal: Molecular pharmacology20060301

Title: NOD2/CARD15 mediates induction of the antimicrobial peptide human beta-defensin-2.

Journal: The Journal of biological chemistry20060127

Title: BK-induced cytosolic phospholipase A2 expression via sequential PKC-delta, p42/p44 MAPK, and NF-kappaB activation in rat brain astrocytes.

Journal: Journal of cellular physiology20060101

Title: Synthesis and anti-viral activity of a series of sesquiterpene lactones and analogues in the subgenomic HCV replicon system.

Journal: Bioorganic & medicinal chemistry20060101

Title: Potent inhibition of human telomerase by helenalin.

Journal: Cancer letters20050928

Title: Polysaccharide purified from Ganoderma lucidum induced activation and maturation of human monocyte-derived dendritic cells by the NF-kappaB and p38 mitogen-activated protein kinase pathways.

Journal: Journal of leukocyte biology20050801

Title: Activation of nuclear factor-kappaB contributes to induction of death receptors and apoptosis by the synthetic retinoid CD437 in DU145 human prostate cancer cells.

Journal: Cancer research20050715

Title: Apoptosis induction by a novel retinoid-related molecule requires nuclear factor-kappaB activation.

Journal: Cancer research20050601

Title: Induction of human leukemia HL-60 cell differentiation via a PKC/ERK pathway by helenalin, a pseudoguainolide sesquiterpene lactone.

Journal: European journal of pharmacology20050328

Title: Involvement of p42/p44 MAPK, JNK, and NF-kappaB in IL-1beta-induced ICAM-1 expression in human pulmonary epithelial cells.

Journal: Journal of cellular physiology20050201

Title: The trypanocidal effect of sesquiterpene lactones helenalin and mexicanin on cultured epimastigotes.

Journal: The Journal of parasitology20050201

Title: Intracellular signalings underlying bradykinin-induced matrix metalloproteinase-9 expression in rat brain astrocyte-1.

Journal: Cellular signalling20041001

Title: New chromanone acids with antibacterial activity from Calophyllum brasiliense.

Journal: Journal of natural products20040401

Title: Pseudoguaianolide sesquiterpene lactones with high activities against the human malaria parasite Plasmodium falciparum.

Journal: Phytotherapy research : PTR20040201

Title: Influence of helenanolide-type sesquiterpene lactones on gene transcription profiles in Jurkat T cells and human peripheral blood cells: anti-inflammatory and cytotoxic effects.

Journal: Biochemical pharmacology20031201

Title: Regulation of microglial inflammatory response by histone deacetylase inhibitors.

Journal: Journal of neurochemistry20031001

Title: Characterization of the molecular events following impairment of NF-kappaB-driven transcription in neurons.

Journal: Brain research. Molecular brain research20021230

Title: Anti-trypanosomal activity of helenalin and some structurally related sesquiterpene lactones.

Journal: Planta medica20020801

Title: Inhibitory effects of helenalin and related compounds on 5-lipoxygenase and leukotriene C(4) synthase in human blood cells.

Journal: Biochemical pharmacology20011001

Title: Helenalin triggers a CD95 death receptor-independent apoptosis that is not affected by overexpression of Bcl-x(L) or Bcl-2.

Journal: Cancer research20010801

Title: The influence of glutathione and cysteine levels on the cytotoxicity of helenanolide type sesquiterpene lactones against KB cells.

Journal: Bioorganic & medicinal chemistry20010801

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