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Aloin

Cat No.:V10841 Purity: ≥98%
Aloin (Aloin-A; Barbaloin-A) is a natural anti-tumor anthraquinone glycoside with iron chelating activity.
Aloin
Aloin Chemical Structure CAS No.: 1415-73-2
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
100mg
250mg
500mg
Other Sizes

Other Forms of Aloin:

  • Aloin B
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Aloin (Aloin-A; Barbaloin-A) is a natural anti-tumor anthraquinone glycoside with iron chelating activity.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
The expression of osteoblast differentiation genes, Bmp-2, Runx2, and collagen 1a is enhanced in a dose-dependent manner by aloin (0.01-1 μM; 10 d) [3]. MC3T3-E1 cells are stimulated to differentiate into osteoblasts by aloin (0.05 μM; 10 d) via the Wnt and Bmp signaling pathways mediated by MAPK [3]. In MC3T3-E1 cells, aloin (0.05 μM; 10 days) boosts ALP activity [3]. Aloe glycoside (10-80 μg/mL; 4.5 hours) attenuates intracellular ROS generation and increases cell survival after biaxial stretch injury (SI), which suppresses alterations in the mitochondrial membrane potential of mouse brain vascular endothelial cells (EC). [4].
ln Vivo
Aloin (10-30 mg/kg; single dosage; intraperitoneally given 30 minutes before TBI injury) reduces cerebral edema produced by traumatic brain injury (TBI) via regulating cortical impact injury in rats. Aloe glycoside demonstrates anti-oxidative stress and anti-apoptotic effects in mouse brain capillary endothelial cells [4].
References

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

[3]. 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.

[4]. Anthraquinone Glycoside Aloin Induces Osteogenic Initiation of MC3T3-E1 Cells: Involvement of MAPK Mediated Wnt and Bmp Signaling. Biomol Ther (Seoul). 2016 Mar 1;24(2):123-3.

[5]. Aloin Protects Against Blood-Brain Barrier Damage After Traumatic Brain Injury in Mice. Neurosci Bull. 2020 Jun;36(6):625-638.

Additional Infomation
Aloin A is 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 diastereoisomer). It has a role as a metabolite and a laxative. It is a C-glycosyl compound, a member of anthracenes, a cyclic ketone and a member of phenols.
Barbaloin has been reported in Aloe ferox, Aloe africana, and other organisms with data available.
See also: Aloe Vera Leaf (part of); Frangula purshiana Bark (part of); Aloin (annotation moved to).
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C21H22O9
Molecular Weight
418.3940
Exact Mass
418.126
CAS #
1415-73-2
Related CAS #
Aloin B;28371-16-6
PubChem CID
12305761
Appearance
Light yellow to yellow solid powder
Density
1.6±0.1 g/cm3
Boiling Point
752.6±60.0 °C at 760 mmHg
Melting Point
148-149ºC
Flash Point
268.0±26.4 °C
Vapour Pressure
0.0±2.6 mmHg at 25°C
Index of Refraction
1.741
LogP
1.86
Hydrogen Bond Donor Count
7
Hydrogen Bond Acceptor Count
9
Rotatable Bond Count
3
Heavy Atom Count
30
Complexity
630
Defined Atom Stereocenter Count
6
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
InChi Key
AFHJQYHRLPMKHU-OSYMLPPYSA-N
InChi Code
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
Chemical 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
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~125 mg/mL (~298.76 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (4.97 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (4.97 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.3901 mL 11.9506 mL 23.9011 mL
5 mM 0.4780 mL 2.3901 mL 4.7802 mL
10 mM 0.2390 mL 1.1951 mL 2.3901 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

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What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Biological Data
  • Cytotoxicity and cell viability profile of aloin: MC3T3-E1 cells were treated with different doses ofaloin for 10 days and assessed by LDH assay for cytotoxicity (A), and MTT assay for cell viability (B) and cell proliferation (C). The data represent mean ± SD of three experiments. *p<0.05 vs control cells, **p<0.05 vs 0.05 μM aloin group.[4]. Anthraquinone Glycoside Aloin Induces Osteogenic Initiation of MC3T3-E1 Cells: Involvement of MAPK Mediated Wnt and Bmp Signaling. Biomol Ther (Seoul). 2016 Mar 1;24(2):123-3.
  • Aloin increased the ALP activity in MC3T3-E1 cells (A) and human adult adipose derived stem cells (hADSC) (B). Cells treated with aloin were fixed and incubated in ALP substrate buffer for 30 min. Theabsorbance at 405 nm was measured as the p-nitrophenol released in nmol using a microplate reader Valueson y-axis represents the nmol ALP production (nmol/ugm protein). The data represent mean ± SD of threeexperiments. *p<0.05 vs control cells. (C) MC3T3-E1 cells treated with 0.05 μM aloin for 10 days were stained for ALP content. ALP in the form of blue droplets were monitored in microscope and photographed using Olympus microscope (Model # 1X73).[4]. Anthraquinone Glycoside Aloin Induces Osteogenic Initiation of MC3T3-E1 Cells: Involvement of MAPK Mediated Wnt and Bmp Signaling. Biomol Ther (Seoul). 2016 Mar 1;24(2):123-3.
  • Effect of aloin on osteogenic marker genes and proteins. (A) Total RNA isolated from MC3T3-E1cells treated with different doses of aloin was subjected to reverse transcription polymerase chain reactionusing specific primers. The band intensities were normalized to the housekeeping gene, GAPDH. The datarepresent mean ± SD of triplicate determinations. *p<0.05 vs. control cells. (B) Relative protein expressions of (a) BMP-2, (b) RunX 2, (c) Collagen 1a, (d) Osteopontin, (e) Osterix and (f) Osteoprotegerin (OPG) wereassessed by WB analysis. β-actin was used as housekeeping control. Data represents the results of threeindependent experiments. Level of significance was calculated at *p<0.05 vs. control cells.[4]. Anthraquinone Glycoside Aloin Induces Osteogenic Initiation of MC3T3-E1 Cells: Involvement of MAPK Mediated Wnt and Bmp Signaling. Biomol Ther (Seoul). 2016 Mar 1;24(2):123-3.
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