CAS 1415-73-2|Aloin

Introduction：Basic information about CAS 1415-73-2|Aloin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Aloin BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Articles32
7. Synonyms

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	ChineseUSA	Flash Point	268.0±26.4 °C
Symbol	GHS07	Signal Word	Warning

Names

Name	aloin A
Synonym	More Synonyms

Aloin BiologicalActivity

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	Signaling Pathways >>Others >>OthersResearch Areas >>CancerNatural Products >>Quinones
References	[1]. Pan Q, et al. Inhibition of the angiogenesis and growth of Aloin in human colorectal cancer in vitro and in vivo. Cancer Cell Int. 2013 Jul 12;13(1):69. [2]. Tabolacci C, et al. Aloin enhances cisplatin antineoplastic activity in B16-F10 melanoma cells by transglutaminase-induced differentiation. Amino Acids. 2013 Jan;44(1):293-300. [3]. Cui Y, et al. Aloin protects against chronic alcoholic liver injury via attenuating lipid accumulation, oxidative stress and inflammation in mice. Arch Pharm Res. 2014 Dec;37(12):1624-33.

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

Signaling Pathways >>Others >>OthersResearch Areas >>CancerNatural Products >>Quinones

References

[1]. Pan Q, et al. Inhibition of the angiogenesis and growth of Aloin in human colorectal cancer in vitro and in vivo. Cancer Cell Int. 2013 Jul 12;13(1):69.

[2]. Tabolacci C, et al. Aloin enhances cisplatin antineoplastic activity in B16-F10 melanoma cells by transglutaminase-induced differentiation. Amino Acids. 2013 Jan;44(1):293-300.

[3]. Cui Y, et al. Aloin protects against chronic alcoholic liver injury via attenuating lipid accumulation, oxidative stress and inflammation in mice. Arch Pharm Res. 2014 Dec;37(12):1624-33.

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
InChIKey	AFHJQYHRLPMKHU-OSYMLPPYSA-N
SMILES	O=C1c2c(O)cccc2C(C2OC(CO)C(O)C(O)C2O)c2cc(CO)cc(O)c21
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
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

Articles32

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.

J. 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

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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