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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H22O9
Molecular Weight 394.3726
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALOESIN

SMILES

CC(=O)CC1=CC(=O)C2=C(O1)C([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=C(O)C=C2C

InChI

InChIKey=HKIKAXXIWJHWLY-ZIIYPAMZSA-N
InChI=1S/C19H22O9/c1-7-3-10(22)14(19-17(26)16(25)15(24)12(6-20)28-19)18-13(7)11(23)5-9(27-18)4-8(2)21/h3,5,12,15-17,19-20,22,24-26H,4,6H2,1-2H3/t12-,15-,16+,17-,19+/m1/s1

HIDE SMILES / InChI

Molecular Formula C19H22O9
Molecular Weight 394.3726
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Aloesin is a chromone derivative isolated from aloe vera. It has many biological effects, such as wound and burn healing properties, and antioxidant, free radical scavenging, anti-inflammatory, and immunomodulatory effects. Aloesin has been shown to be a potent and selective inhibitor of tyrosinase. It exhibited direct inhibitory effects on melanogenesis. Aloesin treatment showed pigmentation suppression in a dose-dependent manner. Thus, aloesin may be used as an agent that inhibits melanin formation induced by UV radiation. Aloesin is thought to be one of the active ingredients in regards to the anti-diabetic activity of Aloe. Aloesin exerts its anticancer effect through the MAPK signaling pathway. It is a novel therapeutic drug for ovarian cancer treatment.

Approval Year

PubMed

PubMed

TitleDatePubMed
Aloesin and arbutin inhibit tyrosinase activity in a synergistic manner via a different action mechanism.
1999 Jun
Antioxidant, free radical scavenging and anti-inflammatory effects of aloesin derivatives in Aloe vera.
2002 Nov
Modulation of melanogenesis by aloesin: a competitive inhibitor of tyrosinase.
2002 Oct
Aloesin inhibits hyperpigmentation induced by UV radiation.
2002 Sep
Aloesin Suppresses Cell Growth and Metastasis in Ovarian Cancer SKOV3 Cells through the Inhibition of the MAPK Signaling Pathway.
2017
Patents

Sample Use Guides

In Vivo Use Guide
100 mg ⁄ g vehicle, four times daily for 15 days.
Route of Administration: Topical
In Vitro Use Guide
Aloesin did not induce reverse mutations in Salmonella typhimurium and Escherichia coli at any of the tested dose levels up to 10,000 ug/plate. Similarly, aloesin did not increase the incidence of chromosome aberrations when incubated with Chinese hamster lung cells at any of the tested concentrations up to 10,000 ug/mL.
Substance Class Chemical
Created
by admin
on Tue Oct 22 13:37:11 UTC 2019
Edited
by admin
on Tue Oct 22 13:37:11 UTC 2019
Record UNII
Y27M69Y8ES
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALOESIN
INCI   MI  
INCI  
Official Name English
ALOESIN [MI]
Common Name English
ALOE RESIN B
Common Name English
NSC-631262
Code English
ALOESIN [INCI]
Common Name English
4H-1-BENZOPYRAN-4-ONE, 8-.BETA.-D-GLUCOPYRANOSYL-7-HYDROXY-5-METHYL-2-(2-OXOPROPYL)-
Common Name English
Code System Code Type Description
MERCK INDEX
M1571
Created by admin on Tue Oct 22 13:37:11 UTC 2019 , Edited by admin on Tue Oct 22 13:37:11 UTC 2019
PRIMARY Merck Index
PUBCHEM
160190
Created by admin on Tue Oct 22 13:37:11 UTC 2019 , Edited by admin on Tue Oct 22 13:37:11 UTC 2019
PRIMARY
MESH
C069868
Created by admin on Tue Oct 22 13:37:11 UTC 2019 , Edited by admin on Tue Oct 22 13:37:11 UTC 2019
PRIMARY
CAS
30861-27-9
Created by admin on Tue Oct 22 13:37:11 UTC 2019 , Edited by admin on Tue Oct 22 13:37:11 UTC 2019
PRIMARY
EPA CompTox
30861-27-9
Created by admin on Tue Oct 22 13:37:11 UTC 2019 , Edited by admin on Tue Oct 22 13:37:11 UTC 2019
PRIMARY