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1415-73-2 molecular structure
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(10S)-1,8-dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-9,10-dihydroanthracen-9-one

ChemBase ID: 72999
Molecular Formular: C21H22O9
Molecular Mass: 418.39398
Monoisotopic Mass: 418.12638228
SMILES and InChIs

SMILES:
[C@@H]1(O[C@H]([C@@H]([C@H]([C@@H]1O)O)O)[C@H]1c2c(C(=O)c3c1cc(cc3O)CO)c(ccc2)O)CO
Canonical SMILES:
OCc1cc(O)c2c(c1)[C@@H]([C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)c1c(C2=O)c(O)ccc1
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-OSYMLPPYSA-N

Cite this record

CBID:72999 http://www.chembase.cn/molecule-72999.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(10S)-1,8-dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-9,10-dihydroanthracen-9-one
IUPAC Traditional name
(10S)-1,8-dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-9,10-dihydroanthracen-9-one
(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
Synonyms
Barbaloin
Barbaloin
Aloin(Barbaloin)
1,8-Dihydroxy-10-(β-D-glucopyranosyl)-3-(hydroxymethyl)-9(10H)-anthracenone
10-β-D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone
Aloin A
Aloin
CAS Number
1415-73-2
EC Number
215-808-0
MDL Number
MFCD00151160
Beilstein Number
6077558
PubChem SID
24890427
162037919
24891938
PubChem CID
12305761

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 9.505504  H Acceptors
H Donor LogD (pH = 5.5) 0.41494715 
LogD (pH = 7.4) 0.4116161  Log P 0.41498974 
Molar Refractivity 103.7931 cm3 Polarizability 40.31564 Å3
Polar Surface Area 167.91 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
pyridine: soluble50 mg/mL, clear, dark red expand Show data source
Storage Condition
-20°C expand Show data source
RTECS
LZ6520000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
26-36 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
2-8°C expand Show data source
Mechanism of Action
Increase prostaglandin synthesis expand Show data source
Na+, K(+)-adenosine triphosphatase (ATPase) inhibitor expand Show data source
Purity
~50% expand Show data source
≥97% expand Show data source
Salt Data
Free Base expand Show data source
Biological Source
Constit. of various Aloe spp. expand Show data source
from Aloe barbadensis Miller leaves expand Show data source
from Curacao aloe expand Show data source
Loss on Drying
≤5% loss on drying expand Show data source
Application(s)
Laxative expand Show data source
Purgative expand Show data source
Empirical Formula (Hill Notation)
C21H22O9 expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich
Selleck Chemicals - S2375 external link
Research Area: Cancer
Biological Activity:
Aloin(Barbaloin) is a potent tyrosinase inhibitor with an IC50 of 97 µM for HeLaS3 cells. It is used as a stimulant-laxative, treating constipation by inducing bowel movements.It also shows a pronounced antiproliferative effect at physiological concentration, causes cell cycle arrest in the S phase, and markedly increases HeLaS3 cell apoptosis (to 24%). In the concentration range of 20-100 µM, its action was accompanied by remarkable changes in the activity of almost all antioxidant enzymes: MnSOD activity was increased many fold, while CuZnSOD and iNOS activities were inhibited. Moreover, inhibition of CuZnSOD was shown to occur by direct aloin interaction with the enzyme. [1][2]
Sigma Aldrich - A0451 external link
Biochem/physiol Actions
Purgative activity in rats requires activation by Eubacterium sp. strain BAR or similar intestinal anaerobe, presumably by conversion to aloe-emodin anthrone.1
Sigma Aldrich - B6906 external link
Application
Aloin, a natural mixed diastereomer (A/B) anthracycline from aloe plant, is studied as an antineoplastic agent that enhances melanogenesis and transglutaminase activity. Aloin A is used as a stabilizer in the preparation of gold and silver nanoparticles.
Biochem/physiol Actions
Purgative activity in rats requires activation by Eubacterium sp. strain BAR or similar intestinal anaerobe, presumably by conversion to aloe-emodin anthrone.1
Sigma Aldrich - 06088 external link
Biochem/physiol Actions
Purgative activity in rats requires activation by Eubacterium sp. strain BAR or similar intestinal anaerobe, presumably by conversion to aloe-emodin anthrone.1

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Ni??iforovi?? A et al. Cancer Biol Ther. 2007 Aug;6(8):1200-5.
  • • 1. Akao T, Che QM, Kobashi K, Hattori M, Namba T.
  • • A purgative action of barbaloin is induced by Eubacterium sp. strain BAR, a human intestinal anaerobe, capable of transforming barbaloin to aloe-emodin anthrone. Biol Pharm Bull. 1996 Jan;19(1):136-8.
  • • 2. Ishii Y, Tanizawa H, Takino Y. Studies of aloe. III. Mechanism of cathartic effect. (2). Chem Pharm Bull (Tokyo). 1990 Jan;38(1):197-200.
  • • 3. Capasso F, Mascolo N, Autore G, Duraccio MR. Effect of indomethacin on aloin and 1,8 dioxianthraquinone-induced production of prostaglandins in rat isolated colon.
  • • Prostaglandins. 1983 Oct;26(4):557-62.
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PATENTS

PATENTS

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INTERNET

INTERNET

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