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Home> Encyclopedia >   /  Antineoplastic Agents  /  Herbal Extract  /  Pharmaceutical Intermediates  /  Others  /  Organic Intermediate
Aloin structure
Aloin structure

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
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.
1. Names and Identifiers
1.1 Name
Aloin
1.2 Synonyms

(R)-10-beta-D-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)anthracen-9(10H)-one 1,8-Dihydroxy-10-(&beta 1,8-Dihydroxy-10-(beta-D-glucopyranosyl)-3-(hydroxymethyl)-9(10H)-anthracenone 10-&beta 6-N-benzyladenosine-5' 9(10H)-Anthracenone, 10-&beta 9(10H)-Anthracenone, 10-.beta.-D-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-, (10S)- ALOIN A(BARBALOIN)(P) Aloin/Barbaloin BAR-5' Barbaloin barbaloin from aloe barbadensis*miller leaves barbaloin isomers Barbaloin std. BarbaloinStandard Benzyl-adenosine monophosphate Benzyl-amp -D-glucopyranosyl)-3-(hydroxymethyl)-9(10H)-anthracenone -D-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-, (R)- -D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone -monophosphat N6-Benzyladenosin-5' N6-Benzyladenosine 5' -O-monophosphate -phosphat

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
3.1 Density
1.647 g/cm3
3.2 Melting Point
148-149ºC
3.3 Boiling Point
752.602ºC at 760 mmHg
3.4 Vapour
0mmHg at 25°C
3.5 Refractive Index
1.741
3.6 Flash Point
268ºC
3.7 Appearance
yellow powder
3.8 Chemical Properties
lemon yellow crystalline powder
3.9 Color/Form
Yellow powder
3.10 pKa
7.12±0.40(Predicted)
3.11 Solubility
pyridine: 50?mg/mL, clear, dark red
3.12 Stability
Stable, but light sensitive. Incompatible with bases, strong oxidizing agents. Combustible.
3.13 StorageTemp
2-8°C
3.14 Water Solubility
pyridine: 50 mg/mL, clear, dark red
3. Use and Manufacturing
4.1 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).
4.2 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
4.3 Safety Profile
Poison by subcutaneous andintravenous routes. Moderately toxic by ingestion. Whenheated to decomposition it emits acrid smoke and fumes.A carthartic and purgative.
4.4 Storage
Ambient temperatures.
4.5 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
5.1 Hazard Codes
Xi
5.2 Risk Statements
R36/37/38
5.3 Safety Statements
S26; S36
5.4 Transport
OTH
5.5 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

8. Precursor and Product
9. 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
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