CHEBI:73222 - aloin

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ChEBI Name aloin
ChEBI ID CHEBI:73222
Definition A diastereoisomeric mixture of aloin A (barbaloin) and aloin B (isobarbaloin), which have similar properties. It is a bitter-tasting, yellow-brown colored compound found in the exudate of at least 68 Aloe species at levels of up to 6.6% of leaf dry weight (making between 3% and 35% of the total exudate), and in another 17 species at indeterminate levels. It is used as a stimulant-laxative, treating constipation by inducing bowel movements.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Steve Jupe
Supplier Information ChemicalBook:CB5159244, eMolecules:474218
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Oxygen is a chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and a potent oxidizing agent that readily forms oxides with most elements as well as with other compounds. Oxygen is the most abundant element in Earth's crust, and the third-most abundant element in the universe after hydrogen and helium. At standard temperature and pressure, two oxygen atoms will bind covalently to form dioxygen, a colorless and odorless diatomic gas with the chemical formula O2. Dioxygen gas currently constitutes approximately 20.95% molar fraction of the Earth's atmosphere, though this has changed considerably over long periods of time in Earth's history. Oxygen makes up almost half of the Earth's crust in the form of various oxides such as water, carbon dioxide, iron oxides and silicates. All eukaryotic organisms, including plants, animals, fungi, algae and most protists, need oxygen for cellular respiration, which extracts chemical energy by the reaction of oxygen with organic molecules derived from food and releases carbon dioxide as a waste product. In aquatic animals, dissolved oxygen in water is absorbed by specialized respiratory organs called gills, through the skin or via the gut; in terrestrial animals such as tetrapods, oxygen in air is actively taken into the body via specialized organs known as lungs, where gas exchange takes place to diffuse oxygen into the blood and carbon dioxide out, and the body's circulatory system then transports the oxygen to other tissues where cellular respiration takes place. However in insects, the most successful and biodiverse terrestrial clade, oxygen is directly conducted to the internal tissues via a deep network of airways. Many major classes of organic molecules in living organisms contain oxygen atoms, such as proteins, nucleic acids, carbohydrates and fats, as do the major constituent inorganic compounds of animal shells, teeth, and bone. Most of the mass of living organisms is oxygen as a component of water, the major constituent of lifeforms. Oxygen in Earth's atmosphere is produced by biotic photosynthesis, in which photon energy in sunlight is captured by chlorophyll to split water molecules and then react with carbon dioxide to produce carbohydrates and oxygen is released as a byproduct. Oxygen is too chemically reactive to remain a free element in air without being continuously replenished by the photosynthetic activities of autotrophs such as cyanobacteria, chloroplast-bearing algae and plants. A much rarer triatomic allotrope of oxygen, ozone (O3), strongly absorbs the UVB and UVC wavelengths and forms a protective ozone layer at the lower stratosphere, which shields the biosphere from ionizing ultraviolet radiation. However, ozone present at the surface is a corrosive byproduct of smog and thus an air pollutant. Oxygen was isolated by Michael Sendivogius before 1604, but it is commonly believed that the element was discovered independently by Carl Wilhelm Scheele, in Uppsala, in 1773 or earlier, and Joseph Priestley in Wiltshire, in 1774. Priority is often given for Priestley because his work was published first. Priestley, however, called oxygen "dephlogisticated air", and did not recognize it as a chemical element. The name oxygen was coined in 1777 by Antoine Lavoisier, who first recognized oxygen as a chemical element and correctly characterized the role it plays in combustion. Common industrial uses of oxygen include production of steel, plastics and textiles, brazing, welding and cutting of steels and other metals, rocket propellant, oxygen therapy, and life support systems in aircraft, submarines, spaceflight and diving.
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Formula C21H22O9
Net Charge 0
Average Mass 418.39400
Monoisotopic Mass 418.12638
InChI InChI=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/t13-,14?,17-,19+,20-,21+/m1/s1
InChIKey AFHJQYHRLPMKHU-CGISPIQUSA-N
SMILES [H][C@]1(O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C1c2cccc(O)c2C(=O)c2c(O)cc(CO)cc12
Roles Classification
Biological Role(s): EC 1.14.18.1 (tyrosinase) inhibitor
Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals.
Application(s): laxative
An agent that produces a soft formed stool, and relaxes and loosens the bowels, typically used over a protracted period, to relieve constipation. Compare with cathartic, which is a substance that accelerates defecation. A substances can be both a laxative and a cathartic.
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ChEBI Ontology
Outgoing aloin (CHEBI:73222) has part aloin A (CHEBI:2991)
aloin (CHEBI:73222) has part aloin B (CHEBI:74131)
aloin (CHEBI:73222) has role EC 1.14.18.1 (tyrosinase) inhibitor (CHEBI:59997)
aloin (CHEBI:73222) has role laxative (CHEBI:50503)
aloin (CHEBI:73222) is a diastereoisomeric mixture (CHEBI:60915)
IUPAC Name
(1S)-1,5-anhydro-1-[4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl]-D-glucitol
Synonyms Sources
10-(1',5'-anhydroglucosyl)aloe-emodin-9-anthrone ChemIDplus
10-β-D-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)anthracen-9(10H)-one ChemIDplus
10-β-D-glucopyranosyl-1,8-dihydroxy-3-hydroxymethyl-9(10H)-anthrone ChemIDplus
Manual Xrefs Databases
Aloin Wikipedia
HMDB0035219 HMDB
View more database links
Registry Number Type Source
1443124 Reaxys Registry Number Reaxys
Citations Types Sources
12622939 PubMed citation Europe PMC
17269040 PubMed citation Europe PMC
20933355 PubMed citation Europe PMC
22139409 PubMed citation Europe PMC
22495441 PubMed citation Europe PMC
23569857 PubMed citation Europe PMC
Last Modified
14 June 2013