Aloin

Iupac Name：(10S)-1,8-dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-10H-anthracen-9-one

CAS No.: 1415-73-2

Molecular Weight：418.39400

Modify Date.: 2022-11-01 12:32

Introduction: Aloin is a naturally occurring substance found in various Aloe plant species. Aloin was originally used as a laxative in the treatment of constipation. Recent studies have investigated Aloin as an antineoplastic agent that enhances melanogenesis and transglutaminase activity. View more+

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1. Names and Identifiers

1.1 Name: Aloin
1.2 Synonyms: (10S)-10-β-D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone 10-epi-Aloin B 9(10H)-Anthracenone, 10-β-D-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-, (10S)- 9(10H)-Anthracenone, 10-β-D-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-, (S)- Aloin A Anthrone, 10-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)- Barbaloin Barbaloin A NSC 407305

1.3 CAS No.: 1415-73-2

1.4 CID: 12305761

1.5 EINECS(EC#): 215-808-0; 610-650-2

1.6 Molecular Formula: C21H22O9 (isomer)

1.7 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

1.8 InChkey: AFHJQYHRLPMKHU-OSYMLPPYSA-N

1.9 Canonical Smiles: C1=CC2=C(C(=C1)O)C(=O)C3=C(C2C4C(C(C(C(O4)CO)O)O)O)C=C(C=C3O)CO

1.10 Isomers Smiles: C1=CC2=C(C(=C1)O)C(=O)C3=C([C@H]2[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C=C(C=C3O)CO

2. Properties

2.1 Density: 1.647 g/cm3

2.1 Melting point: 148-149oC

2.1 Boiling point: 752.602oC at 760 mmHg

2.1 Refractive index: 1.741

2.1 Flash Point: 268oC

2.1 Precise Quality: 418.12600

2.1 PSA: 167.91000

2.1 logP: -0.89120

2.1 Solubility: pyridine: 50?mg/mL, clear, dark red

2.2 Appearance: yellow powder

2.3 Storage: Ambient temperatures.

2.4 Chemical Properties: lemon yellow crystalline powder

2.5 Color/Form: Yellow powder

2.6 pKa: 7.12±0.40(Predicted)

2.7 Water Solubility: pyridine: 50?mg/mL, clear, dark red

2.8 Stability: Stable, but light sensitive. Incompatible with bases, strong oxidizing agents. Combustible.

2.9 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A C-glycosyl compound that is beta-D-glucopyranose in which the anomeric hydroxy group is replaced by a 4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl moiety (the 9S dastereoisomer).

3.2 Purification Methods: Aloin forms the monohydrate as lemon yellow crystals on crystallisation from H2O (450g/1.5L) which has a lower m ~70-80o than the anhydrous substance. [Cahn & Simonsen J Chem Soc 2573 1932, Hay & Haynes J Chem Soc 3141 1956.] AloinSupplier

3.3 Usage: Aloin is a naturally occurring substance found in various Aloe plant species. Aloin was originally used as a laxative in the treatment of constipation. Recent studies have investigated Aloin as an antineoplastic agent that enhances melanogenesis and transglutaminase activity.

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S26; S36

4.1 RIDADR: OTH

4.1 Safety Profile: Poison by subcutaneous andintravenous routes. Moderately toxic by ingestion. Whenheated to decomposition it emits acrid smoke and fumes.A carthartic and purgative.

4.2 WGK Germany: 3

4.2 RTECS: LZ6520000

4.2 Toxicity: LDLo orl-cat: 500 mg/kg HBAMAK 4,1298,35

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

6. NMR Spectrum

7. Synthesis Route

1415-73-2Total: 2 Synthesis Route

572-09-8 135 Suppliers

1415-73-2 256 Suppliers

Literatures:
Pharmaceutica Acta Helvetiae, , vol. 27, p. 17,23
Yield: null

6247-99-0 1 Suppliers

1415-73-2 256 Suppliers

Literatures:
Pharmaceutica Acta Helvetiae, , vol. 27, p. 17,23
Yield: null

8. Precursor and Product

precursor:

572-09-8

6247-99-0

product :

10323-20-3

481-72-1

567-95-3

481-74-3

6247-99-0

9. Other Information

9.0 Usage: Aloe exudant, used as a stimulant-laxative

9.1 BRN: 6077558

9.2 Chemical Properties: lemon yellow crystalline powder

9.3 Uses: Aloin is a naturally occurring substance found in various Aloe plant species. Aloin was originally used as a laxative in the treatment of constipation. Recent studies have investigated Aloin as an ant ineoplastic agent that enhances melanogenesis and transglutaminase activity.

9.4 Definition: ChEBI: A C-glycosyl compound that is beta-D-glucopyranose in which the anomeric hydroxy group is replaced by a 4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl moiety (the 9S d astereoisomer).

9.5 Purification Methods: Aloin forms the monohydrate as lemon yellow crystals on crystallisation from H2O (450g/1.5L) which has a lower m ~70-80o than the anhydrous substance. [Cahn & Simonsen J Chem Soc 2573 1932, Hay & Haynes J Chem Soc 3141 1956.]

10. Computational chemical data

Molecular Weight: 418.39400g/mol
Molecular Formula: C₂₁H₂₂O₉
Compound Is Canonicalized: True
XLogP3-AA: -0.1
Exact Mass: 418.12638228
Monoisotopic Mass: 418.12638228
Complexity: 630
Rotatable Bond Count: 3
Hydrogen Bond Donor Count: 7
Hydrogen Bond Acceptor Count: 9
Topological Polar Surface Area: 168
Heavy Atom Count: 30
Defined Atom Stereocenter Count: 6
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceB4PAAAAAAAAAAAAAAAAAAAAAAAAAA0YMEAAAAAAADBQAAAGgAACAAADRSgmAIwBoAABgCIAqBSAAACAAAkIAAIiAEGCMgJNjaCFRKCcUAl4BELmQfI7PzOwAADAAAYAACAAAYAADAAAAAAAAAAAA==