Aloin

Modify Date: 2019-06-11 23:59:08

Aloin Structure
Aloin structure
Common Name Aloin
CAS Number 1415-73-2 Molecular Weight 418.394
Density 1.6±0.1 g/cm3 Boiling Point 752.6±60.0 °C at 760 mmHg
Molecular Formula C21H22O9 Melting Point 148-149ºC
MSDS Chinese USA Flash Point 268.0±26.4 °C
Symbol GHS07
GHS07
Signal Word Warning

 Use of Aloin


Aloin(Aloin-A; Barbaloin-A) is a natural antitumor anthraquinone glycoside with iron chelating and non-atherogenic activities.IC50 value:Target:in vitro: Aloin significantly inhibited HUVECs proliferation, migration and tube formation in vitro. suppressed activation of VEGF receptor (VEGFR) 2 and STAT3 phosphorylation in endothelial cells. In addition, the constitutively activated STAT3 protein, and the expression of STAT3-regulated antiapoptotic (Bcl-xL), proliferative (c-Myc), and angiogenic (VEGF) proteins were also down-regulated in response to AL in human SW620 cancer cells [1]. aloin exerted inhibition of cell proliferation, adhesion and invasion abilities of B16-F10 melanoma cells under non-cytotoxic concentrations. Furthermore, aloin induced melanoma cell differentiation through the enhancement of melanogenesis and transglutaminase activity [2].in vivo: Aloin substantially reduced tumor volumes and weight in vivo mouse xenografts, without obviously toxicity [1]. Aloin (10, 30 mg/kg bw) or vehicle was given by gavage to mice after each alcohol administration. Alcohol elevated the serum transaminases alanine aminotransferase, aspartate aminotransferase, total cholesterol and triglyceride levels which were significantly attenuated by the co-administration of aloin (p < 0.05) [3].

 Names

Name aloin A
Synonym More Synonyms

 Aloin Biological Activity

Description Aloin(Aloin-A; Barbaloin-A) is a natural antitumor anthraquinone glycoside with iron chelating and non-atherogenic activities.IC50 value:Target:in vitro: Aloin significantly inhibited HUVECs proliferation, migration and tube formation in vitro. suppressed activation of VEGF receptor (VEGFR) 2 and STAT3 phosphorylation in endothelial cells. In addition, the constitutively activated STAT3 protein, and the expression of STAT3-regulated antiapoptotic (Bcl-xL), proliferative (c-Myc), and angiogenic (VEGF) proteins were also down-regulated in response to AL in human SW620 cancer cells [1]. aloin exerted inhibition of cell proliferation, adhesion and invasion abilities of B16-F10 melanoma cells under non-cytotoxic concentrations. Furthermore, aloin induced melanoma cell differentiation through the enhancement of melanogenesis and transglutaminase activity [2].in vivo: Aloin substantially reduced tumor volumes and weight in vivo mouse xenografts, without obviously toxicity [1]. Aloin (10, 30 mg/kg bw) or vehicle was given by gavage to mice after each alcohol administration. Alcohol elevated the serum transaminases alanine aminotransferase, aspartate aminotransferase, total cholesterol and triglyceride levels which were significantly attenuated by the co-administration of aloin (p < 0.05) [3].
Related Catalog
References

[1].

[2].

[3].

 Chemical & Physical Properties

Density 1.6±0.1 g/cm3
Boiling Point 752.6±60.0 °C at 760 mmHg
Melting Point 148-149ºC
Molecular Formula C21H22O9
Molecular Weight 418.394
Flash Point 268.0±26.4 °C
Exact Mass 418.126373
PSA 167.91000
LogP 1.86
Vapour Pressure 0.0±2.6 mmHg at 25°C
Index of Refraction 1.741
Stability Stable, but light sensitive. Incompatible with bases, strong oxidizing agents. Combustible.
Water Solubility pyridine: 50 mg/mL, clear, dark red

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
LZ6520000
CHEMICAL NAME :
10-beta-D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymeth yl)-, 9(10H)-anthracenone-, (+)-
CAS REGISTRY NUMBER :
1415-73-2
LAST UPDATED :
199012
DATA ITEMS CITED :
4
MOLECULAR FORMULA :
C21-H22-O9

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
200 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 8(2),314,1982
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig, Ger. Dem. Rep.) Volume(issue)/page/year: 4,1298,1935
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
200 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig, Ger. Dem. Rep.) Volume(issue)/page/year: 4,1298,1935
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Bird - pigeon
DOSE/DURATION :
200 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig, Ger. Dem. Rep.) Volume(issue)/page/year: 4,1298,1935

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H315-H319-H335
Precautionary Statements P261-P305 + P351 + P338
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xi: Irritant;
Risk Phrases R36/37/38
Safety Phrases 26-36
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS LZ6520000

 Synthetic Route

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Aloin Structure

Aloin

利来AGCAS#:1415-73-2

Literature: Pharmaceutica Acta Helvetiae, , vol. 27, p. 17,23

~%

Aloin Structure

Aloin

利来AGCAS#:1415-73-2

Literature: Pharmaceutica Acta Helvetiae, , vol. 27, p. 17,23

 Precursor & DownStream

Precursor  2

DownStream  6

 Articles32

More Articles
The content of secondary phenol metabolites in pruned leaves of Aloe arborescens, a comparison between two methods: leaf exudates and leaf water extract.

J. Nat. Med. 62(4) , 430-5, (2008)

Aloe arborescens plants, originating from the deserts of South Africa, are grown in the Introduction Garden at Sede Boker in the Negev Desert of Israel. In previous studies, we developed agro-technica...

Determination of aloenin, barbaloin and isobarbaloin in aloe species by micellar electrokinetic chromatography.

利来AGJ. Chromatogr. B. Biomed. Sci. Appl. 752(1) , 91-7, (2001)

Aloenin, barbaloin and isobarbaloin in JP Aloe, Aloe barbadensis (Aloe vera) and Aloe arborescens Miller var. natalensis Berger (Aloe arborescens Miller) were determined by micellar electrokinetic chr...

Liquid chromatographic determination of barbaloin (aloin) in foods.

J. Assoc. Off. Anal. Chem. 68(3) , 493-4, (1985)

A simple and rapid liquid chromatographic method is described for the determination of barbaloin (aloin, 10-D-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthraceno ne) in foods. Barbaloin i...

 Synonyms

(1S)-1,5-Anhydro-1-[(9R)-4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl]-D-glucitol
(10R)-10-β-D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone
6077558
EINECS 215-808-0
barbaloin isomers
BAR-5'-monophosphate
N6-Benzyladenosin-5'-phosphat
(10R)-1,8-Dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]-9(10H)-anthracenone
Aloin
10-β-D-Glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone
Benzyl-amp
isobarbaloin
Benzyl-adenosine monophosphate
9(10H)-Anthracenone, 10-β-D-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-, (R)-
MFCD00151160
10-(1',5'-Anhydroglucosyl)-aloe-emodin-9-anthrone
6-N-benzyladenosine-5'-O-monophosphate
N6-Benzyladenosin-5'-monophosphat
N6-Benzyladenosine 5'-Phosphat
D-Glucitol, 1,5-anhydro-1-C-[(9R)-9,10-dihydro-4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9-anthracenyl]-, (1S)-
1,8-Dihydroxy-10-(β-D-glucopyranosyl)-3-(hydroxymethyl)-9(10H)-anthracenone
(1S)-1,5-Anhydro-1-[(9R)-4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydro-9-anthracenyl]-D-glucitol
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