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Showing Compound Cubebin (FDB002600)

Record Information
Version1.0
Creation date2010-04-08 22:05:26 UTC
Update date2020-02-24 19:10:33 UTC
Primary IDFDB002600
Secondary Accession Numbers
  • FDB021694
Chemical Information
FooDB NameCubebin
DescriptionIsolated from unripe fruit of Piper cubeba (cubeb pepper) About 15% of a volatile oil is obtained by distilling cubebs with water. Cubebene, the liquid portion, has the formula C15H24. It is a pale green or blue-yellow viscous liquid with a warm woody, slightly camphoraceous odor. After rectification with water, or on keeping, this deposits rhombic crystals of camphor of cubebs.; Cubeb (Piper cubeba), or tailed pepper, is a plant in genus Piper, cultivated for its fruit and essential oil. It is mostly grown in Java and Sumatra, hence sometimes called Java pepper. The fruits are gathered before they are ripe, and carefully dried. Commercial cubebs consist of the dried berries, similar in appearance to black pepper, but with stalks attached ? the "tails" in "tailed pepper". The dried pericarp is wrinkled, its color ranges from grayish-brown to black. The seed is hard, white and oily. The odor of cubebs is described as agreeable and aromatic. The taste, pungent, acrid, slightly bitter and persistent. It has been described as tasting like allspice, or like a cross between allspice and black pepper.; Cubebin (C10H10O3) is a crystalline substance existing in cubebs, discovered by Eugène Soubeiran and Capitaine in 1839. It may be prepared from cubebene, or from the pulp left after the distillation of the oil. The drug, along with gum, fatty oils, and malates of magnesium and calcium, contains also about 1% of cubebic acid, and about 6% of a resin. The dose of the fruit is 30 to 60 grains, and the British Pharmacopoeia contains a tincture with a dose of 4 to 1 dram.; In Europe, cubeb was one of the valuable spices during the Middle Ages. It was ground as a seasoning for meat or used in sauces. A medieval recipe includes cubeb in making sauce sarcenes, which consists of almond milk and several spices. As an aromatic confectionery, cubeb was often candied and eaten whole.; In traditional Chinese medicine cubeb is used for its alleged warming property. In Tibetan medicine, cubeb (ka ko la in Tibetan) is one of bzang po drug, six fine herbs beneficial to specific organs in the body, with cubeb assigned to the spleen. Cubebin is found in herbs and spices and pepper (spice).
CAS Number18423-69-3
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.047 g/LALOGPS
logP2.54ALOGPS
logP3.18ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)12.17ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.38 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity91.51 m³·mol⁻¹ChemAxon
Polarizability36.44 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H20O6
IUPAC name3,4-bis(2H-1,3-benzodioxol-5-ylmethyl)oxolan-2-ol
InChI IdentifierInChI=1S/C20H20O6/c21-20-15(6-13-2-4-17-19(8-13)26-11-24-17)14(9-22-20)5-12-1-3-16-18(7-12)25-10-23-16/h1-4,7-8,14-15,20-21H,5-6,9-11H2
InChI KeyDIYWRNLYKJKHAM-UHFFFAOYSA-N
Isomeric SMILESOC1OCC(CC2=CC3=C(OCO3)C=C2)C1CC1=CC2=C(OCO2)C=C1
Average Molecular Weight356.3692
Monoisotopic Molecular Weight356.125988372
Classification
Description Belongs to the class of organic compounds known as dibenzylbutyrolactols. These are lignan compounds containing a 3,4-dibenzyloxolan-2-ol moiety.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassFuranoid lignans
Sub ClassTetrahydrofuran lignans
Direct ParentDibenzylbutyrolactols
Alternative Parents
Substituents
  • Dibenzylbutyrolactol
  • Benzodioxole
  • Benzenoid
  • Tetrahydrofuran
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCubebin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-009i-1339000000-11a72c1bb579684dd238Spectrum
Predicted GC-MSCubebin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-007c-9355200000-58b9915031467f1e363dSpectrum
Predicted GC-MSCubebin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0139000000-dbdae8d0ed784a64a8a92016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08g1-0869000000-a57842f4225a1d634d0a2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6t-0930000000-e6b6af605b413e476adc2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-56cf92cfc1408e7d6be92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0019000000-881571ceb71f68ef248b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-1492000000-69b828ecf7edce8dc2c32016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0019000000-b2bea62dd56524b65bac2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0550-0119000000-04bae9b44cac90ee82fb2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06ri-0729000000-25e25a08e8016a60024e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-7442d31f4cb7b9cb1e502021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-0019000000-4a7ed918e3b1fceb0bd42021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0np4-2359000000-a28c20569adca690a7e52021-09-22View Spectrum
NMRNot Available
ChemSpider ID253695
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID287685
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB30682
CRC / DFC (Dictionary of Food Compounds) IDCMQ43-Q:CMQ43-Q
EAFUS IDNot Available
Dr. Duke IDCUBEBINE|BETA-CUBEBINE|(-)-CUBEBIN
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCubebin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Pepper (Spice)Expected but not quantifiedNot AvailableDUKE
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Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).