| Common Name |
Xanthoxylol
| Description |
(-)-Piperitol is found in herbs and spices. (-)-Piperitol is obtained from Zanthoxylum piperitum (Japanese pepper tree) Xanthoxylol belongs to the family of Furofuran Lignans. These are lignans whose structure is based on 1,4-diphenyl-hexahydrofuro[3,4-c]furan skeleton.
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Structure for HMDB29459 (Xanthoxylol)
| Synonyms |
| Value |
Source |
Xanthoxylol, (1R-(1alpha,3alpha,4beta,6aalpha))-isomerMeSH
Xanthoxylol, (1R-(1alpha,3aalpha,4alpha,6aalpha))-isomerMeSH
Xanthoxylol, (1S-(1alpha,3aalpha,4alpha,6aalpha))-isomerMeSH
| Chemical Formlia |
C20H20O6
| Average Molecliar Weight |
356.3692
| Monoisotopic Molecliar Weight |
356.125988372
| IUPAC Name |
4-[4-(2H-1,3-benzodioxol-5-yl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenol
| Traditional Name |
4-[4-(2H-1,3-benzodioxol-5-yl)-hexahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenol
| CAS Registry Number |
54983-95-8
| SMILES |
COC1=C(O)C=CC(=C1)C1OCC2C1COC2C1=CC2=C(OCO2)C=C1
| InChI Identifier |
InChI=1S/C20H20O6/c1-22-17-6-11(2-4-15(17)21)19-13-8-24-20(14(13)9-23-19)12-3-5-16-18(7-12)26-10-25-16/h2-7,13-14,19-21H,8-10H2,1H3
| InChI Key |
VBIRCRCPHNUJAS-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Lignans, neolignans and related compounds
| Sub Class |
Furanoid lignans
| Direct Parent |
Furanoid lignans
| Alternative Parents |
Furofuran lignans
Methoxyphenols
Benzodioxoles
Phenoxy compounds
Methoxybenzenes
Furofurans
Anisoles
Alkyl aryl ethers
1-hydroxy-2-unsubstituted benzenoids
Tetrahydrofurans
Oxacyclic compounds
Dialkyl ethers
Acetals
Hydrocarbon derivatives
| Substituents |
Furanoid lignan
Furofuran lignan skeleton
Methoxyphenol
Benzodioxole
Anisole
Phenoxy compound
Furofuran
Phenol ether
Methoxybenzene
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Tetrahydrofuran
Acetal
Ether
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound
| Molecliar Framework |
Aromatic heteropolycyclic compounds
| External Descriptors |
a lignan (CPD-8921 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
Food
| Biofunction |
Not Available
| Application |
Nutrient
| Cellliar locations |
Cytoplasm
Extracellliar
| Physical Properties |
| State |
Not Available
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point140 – 142 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.033 mg/mLALOGPS
logP2.41ALOGPS
logP2.36ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)9.91ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.38 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity92.42 m3·mol-1ChemAxon
Polarizability36.95 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, Positivesplash10-0a4i-0019000000-376a43a85fa5035f94edView in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, Positivesplash10-0a4i-0069000000-5c2a864618a9a703efc4View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, Positivesplash10-0udr-7900000000-4822173b5c87eb97e641View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, Negativesplash10-0a4i-0109000000-733eed202d45cb9e1d70View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, Negativesplash10-0a4i-0129000000-22d1f36ee3a5107b85d5View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, Negativesplash10-0f6t-3941000000-063a699456a7bf3bf935View in MoNA
| Biological Properties |
| Cellliar Locations |
Cytoplasm
Extracellliar
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB002761
| KNApSAcK ID |
Not Available
| Chemspider ID |
115586
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB29459
| Metagene Link |
HMDB29459
| METLIN ID |
Not Available
| PubChem Compound |
130679
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: Pulchinenoside A
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
|
PMID: 20957046
