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(R)-3-Amino-4-hydroxybutanoic acid

Cat No.:V68320 Purity: ≥98%
(R)-3-Amino-4-hydroxybutanoic acid is a serine analogue.
(R)-3-Amino-4-hydroxybutanoic acid
(R)-3-Amino-4-hydroxybutanoic acid Chemical Structure CAS No.: 16504-56-6
Product category: Amino Acid Derivatives
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
(R)-3-Amino-4-hydroxybutanoic acid is a serine analogue.
(R)-3-Amino-4-hydroxybutanoic acid (L-β-homoserine, CAS 16504-56-6) is a chiral β-amino acid bearing a γ-hydroxyl group. Its molecular formula is C4H9NO3 with a molecular weight of 119.12 g/mol. It is a serine derivative and is also known as (+)-3-amino-4-hydroxybutyric acid. This compound functions as a full agonist at human recombinant ρ1 GABAC receptors and acts as a modulator of GABAA and GABAB receptors, distinguishing it from simple achiral GABA analogs. The enantiopure (R)-form is essential for studies requiring selective GABAB receptor modulation without confounding GABAA activity from the (S)-enantiomer.
Biological Activity I Assay Protocols (From Reference)
Targets
This compound has specific biological targets as a GABA receptor modulator. It is a full agonist at the human recombinant ρ1 GABAC receptor and a modulator of GABAA and GABAB receptors. The (R)-configuration is essential for potent GABAB receptor interaction, with the (R)-enantiomer demonstrating significantly higher inhibitory potency than the (S)-enantiomer in GABAB binding assays. This compound is utilized in neuroscience research to investigate GABAergic neurotransmission.
ln Vitro
Commercial ergot supplements have been made from amino acids and their derivatives. They affect the release of anabolic hormones, the availability of fuel for activity, the ability to think clearly under pressure, and the prevention of muscular damage brought on by exertion. They are regarded as advantageous synergistic food ingredients [1].
In vitro, this compound acts as a full agonist at human recombinant ρ1 GABAC receptors (EC50 19 µM for WT; retains agonism in T244S mutant where (S)-enantiomer is antagonist). It also modulates GABAA and GABAB receptor activity. The compound is used in neuroscience research to investigate GABAergic neurotransmission in in vitro receptor studies. It has superior GABAB binding inhibition vs. the (S)-isomer for unambiguous receptor assignment.
ln Vivo
This compound has been studied in vivo for its effects on GABAergic neurotransmission. It is utilized in neuroscience research to investigate GABAergic neurotransmission in in vivo models of neurological function. The enantiopure (R)-form is essential for studies requiring selective GABAB receptor modulation without confounding GABAA activity from the (S)-enantiomer. The compound has applications in the synthesis of bioactive peptides and studies related to neurotransmitter regulation and metabolic pathways.
Enzyme Assay
In vitro receptor binding assays for (R)-3-Amino-4-hydroxybutanoic acid typically involve testing against GABAA, GABAB, and GABAC receptors. A standard protocol involves using the compound as a tool to study GABAergic neurotransmission in receptor binding studies. The (R)-enantiomer demonstrates superior GABAB binding inhibition vs. the (S)-isomer for unambiguous receptor assignment. It can be used as a full agonist at ρ1 GABAC receptors.
Cell Assay
This compound is not typically used in standard cell-based assays as a therapeutic agent, but rather as a pharmacological tool compound. It is utilized in neuroscience research to investigate GABAergic neurotransmission. It should be stored under appropriate conditions. Purity is typically ≥98%. It is soluble in water and common organic solvents. The product is for research purposes only and is not intended for human or veterinary use.
Animal Protocol
In vivo, this compound is used in neuroscience research to investigate GABAergic neurotransmission in animal models of neurological function. The enantiopure (R)-form is essential for studies requiring selective GABAB receptor modulation. It has applications in the synthesis of bioactive peptides and studies related to neurotransmitter regulation. However, it is not a therapeutic agent itself.
ADME/Pharmacokinetics
Pharmacokinetic properties of (R)-3-Amino-4-hydroxybutanoic acid are not extensively documented as it is not a drug. It is a small molecule (MW 119.12 g/mol) with the formula C4H9NO3. As a GABA receptor modulator, it may have limited bioavailability due to its polar nature. Detailed ADME studies are limited as the compound is primarily used as a research tool.
Toxicity/Toxicokinetics
The toxicity of (R)-3-Amino-4-hydroxybutanoic acid is not extensively documented, as it is a research chemical not intended for human or veterinary use. It should be handled with standard laboratory precautions, including the use of appropriate personal protective equipment and working in a well-ventilated area. The compound is a solid at room temperature. It is not intended for diagnostic, therapeutic, or other medical applications.
References

[1]. Effects of amino acid derivatives on physical, mental, and physiological activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-1144.

Additional Infomation
(3R)-3-amino-4-hydroxybutyric acid is a β-amino acid formed by replacing the amino group at the 3-position and the hydroxyl group at the 4-position of butyric acid. It is a β-amino acid and also a hydroxy monocarboxylic acid.
(R)-3-Amino-4-hydroxybutanoic acid (L-β-homoserine) is a chiral β-amino acid that functions as a full agonist at human recombinant ρ1 GABAC receptors and a modulator of GABAA and GABAB receptors. The enantiopure (R)-form is essential for studies requiring selective GABAB receptor modulation. It is utilized in neuroscience research to investigate GABAergic neurotransmission. This compound is not a pharmaceutical and has no clinical trials or approved therapeutic status.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C4H9NO3
Molecular Weight
119.12
Exact Mass
119.058
CAS #
16504-56-6
PubChem CID
1502076
Appearance
White to off-white solid powder
Density
1.3±0.1 g/cm3
Boiling Point
374.5±32.0 °C at 760 mmHg
Flash Point
180.3±25.1 °C
Vapour Pressure
0.0±1.9 mmHg at 25°C
Index of Refraction
1.511
LogP
-1.15
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
3
Heavy Atom Count
8
Complexity
83.4
Defined Atom Stereocenter Count
1
SMILES
C([C@H](CO)N)C(=O)O
InChi Key
BUZICZZQJDLXJN-GSVOUGTGSA-N
InChi Code
InChI=1S/C4H9NO3/c5-3(2-6)1-4(7)8/h3,6H,1-2,5H2,(H,7,8)/t3-/m1/s1
Chemical Name
(3R)-3-amino-4-hydroxybutanoic acid
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)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 8.3949 mL 41.9745 mL 83.9490 mL
5 mM 1.6790 mL 8.3949 mL 16.7898 mL
10 mM 0.8395 mL 4.1974 mL 8.3949 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

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
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?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

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:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
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
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
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.

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