Basic information
- CAS
57074-51-8- Standard SMILES
C=C1C(=O)O[C@@H]2C[C@@H](C)[C@@H]3C[C@H](O)O[C@@H](O)[C@@]3(C)C[C@H]12- InChIKey
PYINVOHSOZSEPB-DKGLCQEFSA-N- Molecular formula
- C15H22O5
- Average molar mass
- 282.33 g/mol
- Monoisotopic mass
- 282.1467238
Overview
Hymenoxon is a member of oxanes.
Names & identifiers
- Preferred name
- (3aR,4aS,5R,7R,8aS,9R,10aR)-Decahydro-5,7-dihydroxy-4a,9-dimethyl-3-methylenefuro(2',3':5,6)cyclohepta(1,2-c)pyran-2(3H)-one
- IUPAC
- (1S,3R,7R,9R,10S,12R,14R)-12,14-dihydroxy-1,9-dimethyl-4-methylidene-6,13-dioxatricyclo[8.4.0.03,7]tetradecan-5-one
- English name
- HYMENOXON
- Molecular formula
- C15H22O5
- Molecular weight
- 282.33
Names & synonyms
HymenoxonHymenoxoneAYR8B2NT7757377-32-9DTXSID601104051NSC-217313(1S,3R,7R,9R,10S,12R,14R)-12,14-dihydroxy-1,9-dimethyl-4-methylidene-6,13-dioxatricyclo[8.4.0.03,7]tetradecan-5-one(1R,3R,4aS,5R,6aR,9aR,10aS)-1,3-dihydroxy-5,10a-dimethyl-9-methylene-3,4,4a,5,6,6a,9a,10-octahydro-1H-furo(3,4)cyclohepta(5,7-d)pyran-8-one(1R,3R,4aS,5R,6aR,9aR,10aS)-1,3-dihydroxy-5,10a-dimethyl-9-methylene-3,4,4a,5,6,6a,9a,10-octahydro-1H-furo[3,4]cyclohepta[5,7-d]pyran-8-one(1S,3R,7R,9R,10S,12R,14R)-12,14-dihydroxy-1,9-dimethyl-4-methylidene-6,13-dioxatricyclo(8.4.0.03,7)tetradecan-5-oneRefChem:400558DTXCID901535726
Show more names
Furo[2',3':5,6]cyclohepta[1,2-c]pyran-2(3H)-one, decahydro-5,7-dihydroxy-4a,9-dimethyl-3-methylene-, (3aR,4aS,5R,7R,8aS,9R,10aR)-(3aR,8aα,10aα)-3a,4,4a,5,7,8,8a,9,10,10a-Decahydro-5α,7β-dihydroxy-4aβ,9α-dimethyl-3-methylenefuro[2',3':5,6]cyclohepta[1,2-c]pyran-2(3H)-one(3aR,8aS,10aR)-3a,4,4a,5,7,8,8a,9,10,10a-Decahydro-5α,7β-dihydroxy-4aβ,9α-dimethyl-3-methylenefuro[2',3':5,6]cyclohepta[1,2-c]pyran-2(3H)-one
Properties
Computed structural properties
- XLogP
- 1.7
- Topological polar surface area
- 76 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 0
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 448
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Plant Toxins
Physicochemical properties
- Boiling point
- 289 °C · 289°C (estimate)
- Density
- 1.0984 · 1.0984 (rough estimate)
- refractive index
- 1.62 · 1.6200 (estimate)
- FDA UNII
- 8 B2NT77 · AYR8B2NT77
- Hazardous Substances Data
- 57377 · 57377-32-9(Hazardous Substances Data)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Hazards Summary
Emergency treatment: Plants- sesquiterpene lactones; Sesquiterpene lactones are in many plants. They cause toxicity mainly in livestock that eat the plants. Human poisoning cases are extremely rare. Possible symptoms after ingestion include irritation of mucous membranes, dyspnea, pulmonary hemorrhage, tremors, seizures, abdominal pain, and liver injury. [HSDB] Sesquiterpene lactones are a common cause of allergic dermatitis in florists. See Sesquiterpene lactones.
Toxicology
Adverse EffectsNeurotoxin - Other CNS neurotoxin
Natural Pollution Sources
HYMENOXYS ODORATA (BITTERWEED) IS A MAJOR POISONOUS RANGE PLANT THAT IS INDIGENOUS TO TEXAS, NEW MEXICO, COLORADO, OKLAHOMA, ARIZONA AND CALIFORNIA. HYMENOXON IS EXTRACTED FROM THIS PLANT. HYMENOXON WAS FOUND IN HYMENOXYS ODORATA, HELENIUM HOOPSII AND BAILEYA MULTIRADIATA, AND THE HYMENOXON CONTENT WAS RELATED TO THE RELATIVE TOXICITY (TO ANIMALS) OF THE 3 PLANTS.
Non-Human Toxicity Excerpts
NO SIGNIFICANT SEX DIFFERENCES WERE OBSERVED IN HYMENOXON ORAL LD50 VALUES FOR SWISS WHITE MICE. HYMENOXON WAS A DIRECT-ACTING MUTAGEN IN THE SALMONELLA/MAMMALIAN MICROSOME TEST. URINE SAMPLES OBTAINED FROM HYMENOXON-TREATED MICE WERE NEGATIVE FOR MUTAGENIC ACTIVITY WHEN TESTED DIRECTLY AND WHEN INCUBATED WITH BETA GLUCURONIDASE.
HYMENOXONE WAS TESTED FOR GENOTOXICITY USING 6 STRAINS OF BACILLUS SUBTILIS. IT PRODUCED LETHAL DNA DAMAGE IN STRAINS RECA8 AND MC-1. EVIDENTLY, HYMENOXONE IS CAPABLE OF INDUCING REPAIRABLE DNA DAMAGE IN BACTERIA.
THE IP LD50 IN RATS WAS 16.24 MG/KG FOR HYMENOXON. THE TOXICITY OF A SESQUITERPENE LACTONE DEPENDS ON THE NUMBER OF ALKYLATING CENTERS SUCH AS CYCLOPENTENONE, ALPHA-METHYLENE-GAMMA-LACTONE, OR HEMIACETAL MOIETIES IN THE MOLECULE.
Antidote and Emergency Treatment
Chemistry & industry
Pharmacology
Metabolism/MetabolitesTHE SULFHYDRYL GROUP IS NOT THE PRIMARY REACTIVE SITE. HYMENOXON IS EXCRETED AS GLUCURONIDES VIA URINE AND BILE.
Uses & manufacturing
UsesToxic constituent of Hymenoxys odorata (bitterweed), Helenium hoopsii, and Baileya multiradiata (poisonous range plants); [HSDB]
Additional notes
DefinitionChEBI: Hymenoxon is a member of oxanes.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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