Aloin

Title: Aloin
CAS Registry Number: 5133-19-7
CAS Name: 10-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone
Additional Names: 1,8-dihydroxy-3-hydroxymethyl-10-(6-hydroxymethyl-3,4,5-trihydroxy-2-pyranyl)anthrone; 10-(1¢,5¢-anhydroglucosyl)-aloe-emodin-9-anthrone; barbaloin
Molecular Formula: C21H22O9
Molecular Weight: 418.39
Percent Composition: C 60.28%, H 5.30%, O 34.42%
Literature References: Isoln from various species of aloe (Cape, Uganda and Socotrine): Léger, Ann. Chim. 6, 318 (1916); 8, 265 (1918); Cahn, Simonsen, J. Chem. Soc. 1932, 2573; Rosenthaler, Arch. Pharm. 270, 214 (1932); Mühlemann, Pharm. Acta Helv. 27, 17 (1952); Böhme, Bertram, Arch. Pharm. 288, 510 (1955). The molecule is built from aloe-emodin, q.v., and from glucose. Structure: Hay, Haynes, J. Chem. Soc. 1956, 3141.
Properties: Lemon-yellow crystals, mp 148-149°. Quickly forms a monohydrate, mp 70-80°. Slight odor of aloe; bitter taste. Solubility at 18°: 57% in pyridine, 7.3% in glacial acetic acid, 5.4% in methanol, 3.2% in acetone, 2.8% in methyl acetate, 1.9% in ethanol, 1.8% in water, 1.6% in propanol, 0.78% in ethyl acetate, 0.27% in isopropanol. Very slightly soluble in isobutanol, chloroform, carbon disulfide, ether. Incompatible with alkali hydroxides, tannin, ferric chloride.
Melting point: mp 148-149°; monohydrate, mp 70-80°
Therap-Cat: Cathartic.
Therap-Cat-Vet: Purgative.
Keywords: Laxative/Cathartic.
Alosetron Aloxidone Aloxiprin alpha-(alpha-Aminopropyl)benzyl Alcohol alpha,alpha,beta-Trichloro-n-butyraldehyde

Aloin
Aloin structure.png
Aloin.jpg
Systematic (IUPAC) name
Aloin A: (10S)-10-Glucopyranosyl-1,8-dihydroxy-
3-(hydroxymethyl)-9(10H)-anthracenone
Clinical data
Legal status  ?
Routes Oral
Identifiers
CAS number 8015-61-0 N
ATC code None
PubChem CID 313325
ChemSpider 14269 YesY
UNII W41H6S09F4 YesY
ChEBI CHEBI:73222 N
ChEMBL CHEMBL497001 N
Chemical data
Formula C21H22O9 
Mol. mass 418.39
Physical data
Melt. point 148 °C (298 °F) (70–80 °C for monohydrate)
 N (what is this?)  (verify)

Aloin, also known as Barbaloin,[1] 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 total 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.[2] 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, because they may be carcinogenic and more data is needed to establish otherwise.[3] 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.