Record Information
Version1.0
Creation date2010-04-08 22:10:57 UTC
Update date2018-05-29 01:08:22 UTC
Primary IDFDB013867
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAloin
DescriptionConstituent of various Aloe subspecies Aloin extracted from natural sources is a mixture of two diastereomers, termed aloin A (also called barbaloin) and aloin B (or isobarbaloin), which have similar chemical properties. Aloin is an anthraquinone glycoside, meaning that its anthraquinone skeleton has been modified by the addition of a sugar molecule. Anthraquinones are a common family of naturally occurring yellow, orange, and red pigments of which many have cathartic properties, attributes shared by aloin. Aloin is related to aloe emodin, which lacks a sugar group but shares aloin's biological properties.; Aloin, also known as Barbaloin [Reynolds, Aloes - The genus Aloe, 2004], is a bitter, yellow-brown colored compound noted in the exudate of at least 68 Aloe species at levels from 0.1 to 6.6% of leaf dry weight (making between 3% and 35% of the toal exudate) (Groom & Reynolds, 1987), and in another 17 species at indeterminate levels [Reynolds, 1995b]. It is used as a stimulant-laxative, treating constipation by inducing bowel movements. The compound is present in what is commonly referred to as the aloe latex that exudes from cells adjacent to the vascular bundles, found under the rind of the leaf and in between it and the gel. When dried, it has been used as a bittering agent in commerce (alcoholic beverages) [21 CFR 172.510. Scientific names given include Aloe perryi, A. barbadensis (= A. vera), A. ferox, and hybrids of A. ferox with A. africana and A. spicata.]. Aloe is listed in federal regulations as a natural substance that may be ?safely used in food? when used ?in the minimum quantity required to produce their intended physical or technical effect and in accordance with all the principles of good manufacturing practice.? This food application is generally limited to use in quite small quantities as a flavoring in alcoholic beverages and may usually be identified only as a ?natural flavor.?; In May 2002, the U.S. Food and Drug Administration (FDA) issued a ruling that aloe laxatives are no longer generally recognized as safe (GRAS) and effective, meaning that aloin-containing products are no longer available in over-the-counter drug products in the United States. Aloe vera leaf latex is a concentrate of an herb or other botanical, and so meets the statutory description of an ingredient that may be used in dietary supplements.
CAS Number8015-61-0
Structure
Thumb
Synonyms
SynonymSource
10-(1',5'-Anhydroglucosyl)aloe-emodin-9-anthroneHMDB
10-b-D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone, 9ciHMDB
Aloin aHMDB
AloinumHMDB
BarbaloinHMDB
CafaloinHMDB
JafaloinHMDB
SocaloinHMDB
UgandaloinHMDB
AlloinMeSH
Aloin bMeSH
AloinMeSH
10-b-D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone, 9CIdb_source
Aloin [ban]biospider
Predicted Properties
PropertyValueSource
Water Solubility2.63 g/LALOGPS
logP-0.49ALOGPS
logP0.41ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)9.51ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area167.91 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity103.79 m³·mol⁻¹ChemAxon
Polarizability40.8 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H22O9
IUPAC name1,8-dihydroxy-3-(hydroxymethyl)-10-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-9,10-dihydroanthracen-9-one
InChI IdentifierInChI=1S/C21H22O9/c22-6-8-4-10-14(21-20(29)19(28)17(26)13(7-23)30-21)9-2-1-3-11(24)15(9)18(27)16(10)12(25)5-8/h1-5,13-14,17,19-26,28-29H,6-7H2
InChI KeyAFHJQYHRLPMKHU-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(C(O)C(O)C1O)C1C2=C(C(O)=CC=C2)C(=O)C2=C1C=C(CO)C=C2O
Average Molecular Weight418.394
Monoisotopic Molecular Weight418.126382302
Classification
Description belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassAnthracenes
Sub ClassNot Available
Direct ParentAnthracenes
Alternative Parents
Substituents
  • Anthracene
  • Hexose monosaccharide
  • C-glycosyl compound
  • Glycosyl compound
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monosaccharide
  • Oxane
  • Vinylogous acid
  • Ketone
  • Secondary alcohol
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Aromatic alcohol
  • Organooxygen compound
  • Primary alcohol
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 60.28%; H 5.30%; O 34.42%DFC
Melting Point148 °C (298 °F) (70-80 °C for monohydrate)
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pki-3419100000-2b971eeafcd6d6cbae3aJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00xr-3710739000-bc8e0506c389a1dc8c94JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090000000-b2c1e88e2f0e1c173d2bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090000000-9d98f95e98ec1c3dfbcdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01p9-0090000000-683d7650547bc0b64290JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0011900000-a5045cd633dc0bf7748eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uyi-2397800000-da3da58bef3b6e8f1690JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0159-2192000000-16a746375d56dd614ac1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014j-1146900000-c5f36a22fe5e5e6e70acJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00rb-6329200000-8e01ecbe8e7987e45ca0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9082000000-fa8afb3f04a27a6a78e4JSpectraViewer
ChemSpider ID277139
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID313325
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35219
CRC / DFC (Dictionary of Food Compounds) IDJJG00-H:JJG00-H
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00002797
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAloin
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
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference