2,2-Dihydroxyacetic acid

Name: 2,2-Dihydroxyacetic acid
Brand: MedChemExpress
SKU: HY-W019724
Rating: 4.5 (1 reviews)

Cat. No.: HY-W019724 Purity: 98.0%: Data Sheet
COA

SDS
Handling Instructions
FAQs
Technical Support

2,2-Dihydroxyacetic acid is an endogenous metabolite, which is the monohydrate of Glyoxylic Acid. 2,2-Dihydroxyacetic acid may participate in the microbial glyoxylate cycle, induce an increase in reactive oxygen species, promote cell differentiation, and modify proteins to form advanced glycation end products (AGEs) (HY-NP165). 2,2-Dihydroxyacetic acid is associated with metabolic diseases such as primary hyperoxaluria.

For research use only. We do not sell to patients.

2,2-Dihydroxyacetic acid Chemical Structure

CAS No. : 563-96-2

Size	Stock	Quantity
Solid + Solvent (Highly Recommended)
10 mM * 1 mL in DMSO ready for reconstitution	In-stock	Estimated Time of Arrival: December 31
Solution
10 mM * 1 mL in DMSO	In-stock	Estimated Time of Arrival: December 31
Solid
10 g	In-stock	Estimated Time of Arrival: December 31
25 g	In-stock	Estimated Time of Arrival: December 31
50 g	In-stock	Estimated Time of Arrival: December 31
100 g	In-stock	Estimated Time of Arrival: December 31
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Based on 1 publication(s) in Google Scholar

Other Forms of 2,2-Dihydroxyacetic acid:

2,2-Dihydroxyacetic acid (Standard) Get quote

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Biological Activity
Purity & Documentation
References
Customer Review

Description

In Vitro

2,2-Dihydroxyacetic acid (0-0.8 mM Glyoxylic Acid, 6 d) shows no cytotoxicity, promotes cell differentiation, upregulates indicators related to mitochondrial biogenesis, and increases the intracellular contents of amino acids such as glycine and serine, as well as metabolites such as citric acid and succinic acid in myogenic differentiation assays of mouse myoblast C2C12 cells^[2].
In the experiment of preparing advanced glycation end products (AGEs), 2,2-Dihydroxyacetic acid (3 mM Glyoxylic Acid; incubated with BSA for 24 h) modifies BSA through Glyoxylic Acid (GA) to yield BSA-GA_red. GA_redinduces reactive oxygen species (ROS) production in human colon cancer cells CaCo-2, mouse microglial cells N11, human astrocytoma cells U373 MG, and human embryonic microglial cells CHME-5. Notably, it induces significantly higher levels of ROS production in brain-derived cell lines, while exerting no inhibitory effect on the growth of all four cell lines^[3].\n

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Western Blot Analysis^[2]

Cell Line:	C2C12 cells
Concentration:	As term as Glyoxylic Acid form: 0 mM, 0.2 mM, 0.4 mM, 0.8 mM
Incubation Time:	6 days
Result:	Did not cause significant cytotoxicity and had no obvious effect on cell viability. Increased the protein expression level of MyHC II in a dose-dependent manner. Significantly increased the protein expression level of citrate synthase (CS) in a dose-dependent manner.

In Vivo

Glyoxylic Acid functions in vivo in the form of its conjugate base, namely Glyoxylate. 2,2-Dihydroxyacetic acid (60-150 mg/kg Glyoxylate; intraperitoneal injection; once daily; 3-15 days) induces renal calcium oxalate monohydrate crystal deposition in mice^[4].
2,2-Dihydroxyacetic acid (1%, 5%, 10% glyoxylate aqueous solution; ad libitum drinking; 3-56 days) does not induce renal stone formation in mice via the oral route^[4].
2,2-Dihydroxyacetic acid (50 mg/kg Glyoxylate; i.p.; once daily; days 3-56) fails to induce renal calculi formation in mice^[4].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:	C57BL/6 male mice (8 weeks old), normal model^[4]
Dosage:	As term as Glyoxylate form: 60 mg/kg (0.81 mmol/kg), intraabdominal injection; 80 mg/kg (1.08 mmol/kg), intraabdominal injection; 100 mg/kg (1.35 mmol/kg), intraabdominal injection; 150 mg/kg (2.03 mmol/kg), intraabdominal injection
Administration:	Intraperitoneal injection, once daily; for 3-15 days.
Result:	At doses above 60 mg/kg induced calcium oxalate monohydrate crystal deposition in the mouse kidneys, which peaked at 6 days and gradually decreased thereafter, with almost no crystals detected at 15 days; the crystals were mainly distributed in the renal tubules at the border between the renal cortex and medulla; the expression of osteopontin (OPN) mRNA and protein was dramatically increased, with OPN localized in renal tubules and stones; urinary pH significantly decreased on day 6, and urinary calcium and oxalate levels increased on day 12 or 15.

Molecular Weight

92.05

Formula

C₂H₄O₄

CAS No.

563-96-2

Appearance

Solid

Color

White to light yellow

SMILES

O=C(C(O)O)O

Structure Classification

Ketones, Aldehydes, Acids

Initial Source

Endogenous metabolite

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

RT, protect from light, stored under nitrogen

In solvent	-80°C	1 year
	-20°C	6 months

Solvent & Solubility

In Vitro:

DMSO : 100 mg/mL (1086.37 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

Preparing
Stock Solutions

Concentration Solvent Mass	1 mg	5 mg	10 mg

1 mM	10.8637 mL	54.3183 mL	108.6366 mL
5 mM	2.1727 mL	10.8637 mL	21.7273 mL
10 mM	1.0864 mL	5.4318 mL	10.8637 mL

View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 1 year; -20°C, 6 months. When stored at -80°C, please use it within 1 year. When stored at -20°C, please use it within 6 months.

Molarity Calculator
Dilution Calculator

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Concentration _(start) × Volume _(start) = Concentration _(final) × Volume _(final)

This equation is commonly abbreviated as: C₁V₁ = C₂V₂

Concentration _(start)

Volume _(start)

Concentration _(final)

Volume _(final)

In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for in vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: ≥ 2.5 mg/mL (27.16 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.
Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
Protocol 2

Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)
Solubility: ≥ 2.5 mg/mL (27.16 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
Protocol 3

Add each solvent one by one: 10% DMSO 90% Corn Oil
Solubility: ≥ 2.5 mg/mL (27.16 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL Corn oil, and mix evenly.

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage

mg/kg

Animal weight
(per animal)

Dosing volume
(per animal)

μL

Number of animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Please enter your animal formula composition:

DMSO +

Tween-80 +

Saline

Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.

The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).

Calculation results:

Working solution concentration: mg/mL

Method for preparing stock solution: mg drug dissolved in μL DMSO (Stock solution concentration: mg/mL).

The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only. If necessary, please contact MedChemExpress (MCE).

Method for preparing in vivo working solution for animal experiments: Take μL DMSO stock solution, add μL . μL , mix evenly, next add μL Tween 80, mix evenly, then add μL Saline.

If the continuous dosing period exceeds half a month, please choose this protocol carefully.

Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.

Purity & Documentation

Purity: 98.0%

Select Batch:

Data Sheet (278 KB) SDS (615 KB)

COA (247 KB) HNMR (149 KB) CNMR (122 KB)

Handling Instructions (2659 KB)

References

[1]. Okada A, et al. Successful formation of calcium oxalate crystal deposition in mouse kidney by intraabdominal glyoxylate injection[J]. Urological research, 2007, 35(2): 89-99.

[2]. Smirnov A Y, et al. Aminocoumaranones as chemiluminescence indicators of the urease activity and hydrogen peroxide[J]. Russian Journal of Bioorganic Chemistry, 2024, 50(1): 260-266.

[3]. Norikura T, et al. Glyoxylic Acid, an α-Keto Acid Metabolite Derived from Glycine, Promotes Myogenesis in C2C12 Cells. Nutrients. 2023 Apr 4;15(7):1763. [Content Brief]

[4]. Schmitt A, et al. Induction of reactive oxygen species and cell survival in the presence of advanced glycation end products and similar structures[J]. Biochimica et Biophysica Acta (BBA)-Molecular Cell Research, 2006, 1763(9): 927-936.

Complete Stock Solution Preparation Table

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg

DMSO	1 mM	10.8637 mL	54.3183 mL	108.6366 mL	271.5915 mL
	5 mM	2.1727 mL	10.8637 mL	21.7273 mL	54.3183 mL
	10 mM	1.0864 mL	5.4318 mL	10.8637 mL	27.1592 mL
	15 mM	0.7242 mL	3.6212 mL	7.2424 mL	18.1061 mL
	20 mM	0.5432 mL	2.7159 mL	5.4318 mL	13.5796 mL
	25 mM	0.4345 mL	2.1727 mL	4.3455 mL	10.8637 mL
	30 mM	0.3621 mL	1.8106 mL	3.6212 mL	9.0531 mL
	40 mM	0.2716 mL	1.3580 mL	2.7159 mL	6.7898 mL
	50 mM	0.2173 mL	1.0864 mL	2.1727 mL	5.4318 mL
	60 mM	0.1811 mL	0.9053 mL	1.8106 mL	4.5265 mL
	80 mM	0.1358 mL	0.6790 mL	1.3580 mL	3.3949 mL
	100 mM	0.1086 mL	0.5432 mL	1.0864 mL	2.7159 mL