Record Information
Version1.0
Creation date2010-04-08 22:04:52 UTC
Update date2018-05-28 22:37:47 UTC
Primary IDFDB001176
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsodulcitol
DescriptionConstituent of many glycosides in plants. Quercetin (main constituent of lemon flavin) and Naringin (from grapefruit-canning wastes) have been used as sources A methylpentose whose L- isomer is found naturally in many plant glycosides and some gram-negative bacterial lipopolysaccharides.; Rhamnose (Rham) is a naturally-occurring deoxy sugar. It can be classified as either a methyl-pentose or a 6-deoxy-hexose. Rhamnose occurs in nature in its L-form as L-rhamnose (6-deoxy-L-mannose). This is unusual, since most of the naturally-occurring sugars are in D-form. Exceptions are the methyl pentoses L-fucose and L-rhamnose and the pentose L-arabinose.; Rhamnose is a component of the outer cell membrane of acid-fast bacteria in the Mycobacterium genus, which includes the organsism that causes tuberculosis. Isodulcitol is found in many foods, some of which are tarragon, sweet basil, garden cress, and coconut.
CAS Number3615-41-6
Structure
Thumb
Synonyms
SynonymSource
6-Deoxy-L-mannoseChEBI
L-(+)-RhamnoseChEBI
L-MannomethyloseChEBI
L-RhaChEBI
L-RhamnoseChEBI
L-RhamnopyranoseKegg
6-Deoxy-L(+)-mannoseHMDB
6-Deoxy-L-mannopyranoseHMDB
6-Deoxy-mannoseHMDB
6-DeoxyhexopyranoseHMDB
6-DeoxyhexoseHMDB
6-DeoxymannoseHMDB
IsodulcitHMDB
IsodulcitolHMDB
L(+)-RhamnoseHMDB
L(+)-Rhamnose monohydrateHMDB
L-(+)-Rhamnose 1-hydrateHMDB
L-(+)-Rhamnose hydrate = 6-deoxy-L-mannose monohydrateHMDB
L-(+)-Rhamnose monohydrateHMDB
L-Rhamnose for biochemistryHMDB
L-Rhamnose monohydrateHMDB
LocaoseHMDB
mono(6-Deoxy-b-L-mannopyranosyl) esterHMDB
mono(6-Deoxy-beta-L-mannopyranosyl) esterHMDB
p-(6-Deoxy-b-L-mannopyranosyl) esterHMDB
p-(6-Deoxy-beta-L-mannopyranosyl) esterHMDB
RhamnopyranoseHMDB
RhamnosemonohydrateHMDB
UDP-RhamnoseHMDB
Uridine 5-pyrophosphateHMDB
Uridine diphosphate rhamnoseHMDB
DeoxymannoseHMDB
Rhamnose, L isomerHMDB
Rhamnose, L-isomerHMDB
RhamnoseMeSH
Lokaosedb_source
Mono(6-deoxy-b-L-mannopyranosyl) esterHMDB
Mono(6-deoxy-beta-L-mannopyranosyl) esterHMDB
P-(6-Deoxy-b-L-mannopyranosyl) esterHMDB
P-(6-Deoxy-beta-L-mannopyranosyl) esterHMDB
Uridine 5-pyroateHMDB
Uridine diate rhamnoseHMDB
Predicted Properties
PropertyValueSource
Water Solubility827 g/LALOGPS
logP-2.4ALOGPS
logP-1.9ChemAxon
logS0.7ALOGPS
pKa (Strongest Acidic)11.3ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area90.15 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity34.38 m³·mol⁻¹ChemAxon
Polarizability15.09 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC18H36O15
IUPAC name(3R,4R,5R,6S)-6-methyloxane-2,3,4,5-tetrol
InChI IdentifierInChI=1S/3C6H12O5/c1-2(7)5-3(8)4(9)6(10)11-5;1-2-3(7)4(8)5(9)6(10)11-2;1-3(8)5(10)6(11)4(9)2-7/h2*2-10H,1H3;2-6,8-11H,1H3
InChI KeyLSOFIIQFGYOXNZ-UHFFFAOYSA-N
Isomeric SMILESCC(O)C(O)C(O)C(O)C=O.CC(O)C1OC(O)C(O)C1O.CC1OC(O)C(O)C(O)C1O
Average Molecular Weight492.4694
Monoisotopic Molecular Weight492.205420482
Classification
Description belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexoses
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 43.90%; H 7.37%; O 48.73%DFC
Melting PointMp 93-95° (hydrate)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +8.9 (H2O, at equilibrium)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-ff79aee2e9ac3a4f53c8View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-23d1bd654495aefbf615View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-ff79aee2e9ac3a4f53c8View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-23d1bd654495aefbf615View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4j-9500000000-cfa9e0d8f1f20b29e5d8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-002r-9346400000-7524daf3b04caf0c441aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0019-9600000000-8cb337afbc2d297157bfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0uy0-9600000000-cb7dbb4d86a5bc544704View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9200000000-89022407246ea7a22497View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03di-0900000000-2196b54a850c456b7ee8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-2196b54a850c456b7ee8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-5daf054ff3eb9127d3caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-0900000000-f7729c93b964e01cb774View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a70-9000000000-2c46a67befe14c31d7a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2900000000-86321b083a11f93bb55bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dj-5900000000-2accd457fe7b58b9b032View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-9e349c8fad042f6a3e99View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID23642
ChEMBL IDNot Available
KEGG Compound IDC00507
Pubchem Compound ID25310
Pubchem Substance IDNot Available
ChEBI ID16055
Phenol-Explorer IDNot Available
DrugBank IDDB01869
HMDB IDHMDB00849
CRC / DFC (Dictionary of Food Compounds) IDHBK38-S:BVJ77-U
EAFUS ID3290
Dr. Duke IDL-RHAMNOSE|RHAMNOSE
BIGG IDNot Available
KNApSAcK IDNot Available
HET ID1CB8
Flavornet IDNot Available
GoodScent IDrw1037731
SuperScent IDNot Available
Wikipedia IDRhamnose
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
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).