EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

(±)-isoalantolactone
8-beta-hydroxyeudesma-4(14),11(13)-dien-12-oic acid gamma-lactone

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Name:(3aR,4aS,8aR,9aR)-8a-methyl-3,5-dimethylidene-3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-2-one
CAS Number: 470-17-7Picture of molecule3D/inchi
FDA UNII: BYH07P620U
Nikkaji Web:J12.027H
Beilstein Number:0013402
XlogP3-AA:3.40 (est)
Molecular Weight:232.32280000
Formula:C15 H20 O2
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Appearance:colorless crystals (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 112.00 °C. @ 760.00 mm Hg
Boiling Point: 364.00 to 365.00 °C. @ 760.00 mm Hg (est)
Vapor Pressure:0.000038 mmHg @ 25.00 °C. (est)
Flash Point: 307.00 °F. TCC ( 152.70 °C. ) (est)
logP (o/w): 3.420
Soluble in:
 alcohol
 water, 35.49 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Isoalantolactone 98%
BOC Sciences
For experimental / research use only.
Isoalantolactone >98%
Odor: characteristic
Use: Isoalantolactone has the capacity to inhibit tumor cell growth through induction of apoptosis. anti-microbial
Capot Chemical
Isoalantolactone
Glentham Life Sciences
Isoalantolactone
 
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
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for (±)-isoalantolactone usage levels up to:
 not for fragrance use.
 
Recommendation for (±)-isoalantolactone flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :73285
National Institute of Allergy and Infectious Diseases:Data
(3aR,4aS,8aR,9aR)-8a-methyl-3,5-dimethylidene-3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-2-one
Chemidplus:0000470177
 
References:
 (3aR,4aS,8aR,9aR)-8a-methyl-3,5-dimethylidene-3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-2-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):73285
Pubchem (sid):135029823
 
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
CHEMBL:View
KEGG (GenomeNet):C09484
HMDB (The Human Metabolome Database):HMDB35934
FooDB:FDB014737
Export Tariff Code:2932.29.6000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
EFSA Update of results on the monitoring of furan levels in food:Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:Read Report
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 elecampane root oil
Search Trop Picture
 inula oculus-christi
Search Trop Picture
 
Synonyms:
iso-alantolactone
(3aR-(3aalpha,4aalpha,8abeta,9aalpha))-decahydro-8a-methyl-3,5-bis(methylene)naphtho(2,3-b)furan-2(3H)-one
 eudesma-4(14),11(13)-dien-12-oic acid, 8-b-hydroxy-, gamma-lactone
isohelenine
8-beta-hydroxyeudesma-4(14),11(13)-dien-12-oic acid gamma-lactone
(3aR,4aS,8aR,9aR)-8a-methyl-3,5-bis(methylene)decahydronaphtho[2,3-b]furan-2(3H)-one
(3aR,4aS,8aR,9aR)-8a-methyl-3,5-dimethylene-decahydro-naphtho[2,3-b]furan-2-one
(3aR,4aS,8aR,9aR)-8a-methyl-3,5-dimethylenedecahydronaphtho[2,3-b]furan-2(3H)-one
(3aR,4aS,8aR,9aR)-8a-methyl-3,5-dimethylidene-3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-2-one
(3aR,4aS,8aR,9aR)-8a-methyl-3,5-dimethylidenedecahydronaphtho[2,3-b]furan-2(3H)-one
 naphtho(2,3-b)furan-2(3H)-one, decahydro-8a-methyl-3,5-bis(methylene)-, (3aR-(3a a,4a a,8a β,9a a))-
 naphtho[2,3-b]furan-2(3H)-one, decahydro-8a-methyl-3, 5-bis(methylene)-, [3aR-(3aa,4aa,8aβ,9aa)]-
 naphtho[2,3-b]furan-2(3H)-one, decahydro-8a-methyl-3,5-bis(methylene)-, (3aR,4aS,8aR,9aR)-
 

Articles:

PubMed:Isoalantolactone inhibits constitutive NF-κB activation and induces reactive oxygen species-mediated apoptosis in osteosarcoma U2OS cells through mitochondrial dysfunction.
PubMed:UPLC/MS/MS method for quantification and cytotoxic activity of sesquiterpene lactones isolated from Saussurea lappa.
PubMed:Simultaneous Determination of Chlorogenic Acid, Caffeic Acid, Alantolactone and Isoalantolactone in Inula helenium by HPLC.
PubMed:Growth Inhibition Effects of Isoalantolactone on K562/A02 Cells: Caspase-dependent Apoptotic Pathways, S Phase Arrest, and Downregulation of Bcr/Abl.
PubMed:Identification of CYP2C19 inhibitors from phytochemicals using the recombinant human enzyme model.
PubMed:A Gas Chromatography-Mass Spectrometry Method for the Determination of Pogostone in Canine Plasma and Its Application to a Pharmacokinetic Study.
PubMed:Simultaneous determination of sesquiterpene lactones isoalantolactone and alantolactone isomers in rat plasma by liquid chromatography with tandem mass spectrometry: application to a pharmacokinetic study.
PubMed:Targeting apoptosis pathways in cancer with alantolactone and isoalantolactone.
PubMed:Sesquiterpene lactones and their derivatives inhibit high glucose-induced NF-κB activation and MCP-1 and TGF-β1 expression in rat mesangial cells.
PubMed:Isoalantolactone inhibits UM-SCC-10A cell growth via cell cycle arrest and apoptosis induction.
PubMed:Reactive oxygen species mediate isoalantolactone-induced apoptosis in human prostate cancer cells.
PubMed:Isoalantolactone, a sesquiterpene lactone, induces apoptosis in SGC-7901 cells via mitochondrial and phosphatidylinositol 3-kinase/Akt signaling pathways.
PubMed:Conformational analysis of antistaphylococcal sesquiterpene lactones from Inula helenium essential oil.
PubMed:Antitumour activities of sesquiterpene lactones from Inula helenium and Inula japonica.
PubMed:Chemical composition of essential oils from a multiple shoot culture of Telekia speciosa and different plant organs.
PubMed:Isoalantolactone induces reactive oxygen species mediated apoptosis in pancreatic carcinoma PANC-1 cells.
PubMed:Isoalantolactone protects against Staphylococcus aureus pneumonia.
PubMed:Antistaphylococcal activity of Inula helenium L. root essential oil: eudesmane sesquiterpene lactones induce cell membrane damage.
PubMed:Nuclear factor kappa B plays a pivotal role in polyinosinic-polycytidylic acid-induced expression of human β-defensin 2 in intestinal epithelial cells.
PubMed:Ultrasound-assisted extraction of alantolactone and isoalantolactone from Inula helenium roots.
PubMed:Structure-activity relationship studies on derivatives of eudesmanolides from Inula helenium as toxicants against Aedes aegypti larvae and adults.
PubMed:Activation of caspases and poly (ADP-ribose) polymerase cleavage to induce apoptosis in leukemia HL-60 cells by Inula racemosa.
PubMed:HPLC determination and NMR structural elucidation of sesquiterpene lactones in Inula helenium.
PubMed:Isoalantolactone from Inula helenium caused Nrf2-mediated induction of detoxifying enzymes.
PubMed:Separation and determination of alantolactone and isoalantolactone in traditional Chinese herbs by capillary electrophoresis.
PubMed:Nrf2-mediated induction of detoxifying enzymes by alantolactone present in Inula helenium.
PubMed:Induction of detoxifying enzyme by sesquiterpenes present in Inula helenium.
PubMed:Simultaneous quantification of eudesmanolides and thymol derivatives from tissues of Inula helenium and I. royleana by reversed-phase high-performance liquid chromatography.
PubMed:Separation and determination of two sesquiterpene lactones in Radix inulae and Liuwei Anxian San by microemulsion electrokinetic chromatography.
PubMed:Constituents of two Flourensia species.
PubMed:Antiproliferative sesquiterpene lactones from the roots of Inula helenium.
PubMed:Anti-trypanosomal activity of helenalin and some structurally related sesquiterpene lactones.
PubMed:Cytotoxic Michael-type amine adducts of alpha-methylene lactones alantolactone and isoalantolactone.
PubMed:Evidence for [2 + 2] photoreaction of alpha-methylene-gamma-butyrolactones with thymine: an explanation for chronic actinic dermatitis to sesquiterpene lactones?
PubMed:Antimycobacterial eudesmanolides from Inula helenium and Rudbeckia subtomentosa.
PubMed:Lignans and sesquiterpene lactones from Artemisia sieversiana and Inula racemosa.
PubMed:In vitro model for contact sensitization: I. Stimulatory capacities of human blood-derived dendritic cells and their phenotypical alterations in the presence of contact sensitizers.
PubMed:A murine in vitro model of allergic contact dermatitis to sesquiterpene alpha-methylene-gamma-butyrolactones.
PubMed:Cross-reaction in allergic contact dermatitis from alpha-methylene-gamma-butyrolactones: importance of the cis or trans ring junction.
PubMed:[Contact eczema caused by Chrysanthemum morifolium Ramat].
PubMed:Contact dermatitis to Alstroemeria.
PubMed:[Gaillardia allergy].
PubMed:Allergic contact dermatitis to methylenelactones. Use of lymphocyte transformation test.
PubMed:The sensitizing capacity of helenin and of two of its main constituents, the sesquiterpene lactones alantolactone and isoalantolactone: a comparison of epicutaneous and intradermal sensitizing methods in different strains of guinea pig.
PubMed:Synthesis of alpha-methylene-gamma-butyrolactones: a structure-activity relationship study of their allergenic power.
PubMed:Allergic contact dermatitis due to sesquiterpene lactones. A comparative study of human and animal sensitivity to alpha-methylene-gamma-butyrolactone and derivatives.
 
Notes:
Constit. of the essential oil of Inula helenium (elecampane)
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