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Z-β-alanine

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Z-β-alanine has been utilized for various synthesis applications including palladium-catalyzed asymmetric allylation of β-diketones, branched linker that can increase the potency of doxorubicin immunoconjugates, and diacridines that intercalate nucleic acids and inhibit DNA synthesis.

Category

CBZ-Amino Acids

Catalog number

BAT-007603

CAS number

2304-94-1

Molecular Formula

C11H13NO4

Molecular Weight

223.20

IUPAC Name

3-(phenylmethoxycarbonylamino)propanoic acid

Synonyms

Z-β-Ala-OH; 3-Z-aminopropanoic acid; Z-beta-Ala-OH; carbobenzyloxy-beta-alanine; N-Cbz-beta-alanine; Cbz-beta-alanine; N-Benzyloxycarbonyl-beta-alanine; Cbz-beta-Ala-OH; N-Carbobenzoxy-beta-alanine; 3-(benzyloxycarbonylamino)propanoic acid; 3-{[(benzyloxy)carbonyl]amino}propanoic acid; Z beta Ala OH; Cbz beta Ala OH

Appearance

White powder

Purity

≥ 99% (HPLC)

Density

1.249±0.06 g/cm3 (Predicted)

Melting Point

101-107 °C

Boiling Point

435.9±38.0 °C (Predicted)

Storage

Store at 2-8 °C

InChI

InChI=1S/C11H13NO4/c13-10(14)6-7-12-11(15)16-8-9-4-2-1-3-5-9/h1-5H,6-8H2,(H,12,15)(H,13,14)

InChI Key

GEVGRLPYQJTKKS-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)COC(=O)NCCC(=O)O

Z-β-alanine, a non-proteinogenic amino acid, finds diverse applications in biochemistry and pharmacology. Here are the key applications presented with high perplexity and burstiness:

Sports Nutrition: Embraced as a dietary supplement in the realm of sports nutrition, Z-β-alanine plays a pivotal role in enhancing athletic prowess. Serving as a precursor to carnosine, it acts as a buffer against lactic acid accumulation in muscles effectively staving off fatigue and bolstering endurance. Athletes and fitness aficionados alike leverage its potential to elevate exercise capacity and optimize training outcomes fueling their quest for peak performance on the field or in the gym.

Pharmaceutical Development: In the sphere of drug development, Z-β-alanine emerges as a promising candidate for driving therapeutic innovation. Its bioactive nature lends itself to the synthesis of novel medications targeting a spectrum of metabolic and neurological disorders. Furthermore its ability to modulate neurotransmitter systems hints at potential applications in addressing mental health conditions like anxiety and depression offering a ray of hope in the realm of pharmacological interventions.

Cosmetic Industry: Within the cosmetic domain, Z-β-alanine shines as a coveted ingredient renowned for its skin-transforming capabilities. Employed for its skin-conditioning prowess, it plays a vital role in formulations aimed at bolstering skin hydration and diminishing the appearance of fine lines and wrinkles. Its knack for enhancing collagen production positions it as a prized asset in anti-aging products promoting skin that exudes vitality and youthfulness a testament to the intersection of science and beauty.

Biochemical Research: In the landscape of scientific inquiry, Z-β-alanine emerges as a cornerstone in unraveling the intricacies of amino acid metabolism and related biochemical pathways. Researchers harness its potential to delve into the enzymatic processes governing its synthesis and breakdown shedding light on the underpinnings of amino acid metabolism. This profound understanding not only enriches our knowledge landscape but also holds the promise of informing therapeutic strategies and shaping nutritional guidelines offering tantalizing possibilities for advancing human health and well-being.

1. N-(benzyloxycarbonyl)glycine esters and amides as new anticonvulsants

M Geurts, J H Poupaert, G K Scriba, D M Lambert J Med Chem. 1998 Jan 1;41(1):24-30. doi: 10.1021/jm970086f.

Glycine is a small neutral amino acid exhibiting weak anticonvulsant activities in vivo. Recently, studies have demonstrated that N-(benzyloxycarbonyl)glycine (1) antagonized seizures superior to glycine in addition to activity in the maximal electroshock (MES) test, a convulsive model where glycine is inactive. In the present study a series of ester and amide derivatives of 1 as well as esters of N-(3-phenylpropanoyl)glycine (5) have been prepared. The compounds were evaluated in the MES test as well as in several chemically induced seizure models. Among the derivatives investigated, N-(benzyloxycarbonyl)glycine benzylamide (16) was the most potent compound exhibiting an anticonvulsant activity in the MES test comparable to the drug phenytoin. Median effective doses (ED50) of 4.8 and 11.6 mg/kg were determined at 30 min and 3 h after i.p. administration, respectively. Compound 16 also effectively suppressed tonic seizures in different chemically induced models such as the strychnine, 3-mercaptopropionic acid, and pentylenetetrazole tests. Moreover, the compound studied here did not show acute neurotoxicity in the rotorod test up to a dose of 150 mg/kg. It is concluded that N-(benzyloxycarbonyl)glycine amides, especially 16, are potent anticonvulsant agents.

2. Anticonvulsant activity of phenytoin-lipid conjugates, a new class of phenytoin prodrugs

G K Scriba, D M Lambert, J H Poupaert J Pharm Pharmacol. 1995 Mar;47(3):197-203. doi: 10.1111/j.2042-7158.1995.tb05778.x.

The anticonvulsant activity of phenytoin-lipid conjugates obtained by covalent binding of 3-hydroxy-methylphenytoin to dimyristoylglycerides via a succinidyl linkage, to 2-(1,3-dimyristoylglyceryl)butyric acid and to 3-myristoyl-2-myristoylmethylpropionic acid was evaluated in the maximal electroshock (MES) test and the seizure threshold test with subcutaneous pentetrazol. The phenytoin-lipid conjugates were less active than the parent drug in the MES test after intraperitoneal administration as suspensions, but exhibited comparable activity when injected as a solution in dimethylsulphoxide. They also protected mice from MES-induced seizures following oral administration of aqueous suspensions of the compounds or when incorporated into emulsions. The anticonvulsant activity could be correlated to in-vitro pancreatic lipase-mediated hydrolysis. The bis-deacyl derivatives were at least as active but in some cases also more toxic than phenytoin. Oral administration of two of the lipid conjugates resulted in a faster onset of the anticonvulsant activity compared with the administration of an equimolar dose of phenytoin itself. All compounds were inactive in the subcutaneous pentetrazol test. It is concluded that the lipids act as prodrugs of phenytoin, which is generated by lipolysis upon oral administration.

3. 3-Hydroxymethylphenytoin valproic acid ester, a new prodrug combining two anticonvulsant drugs

G K Scriba Arch Pharm (Weinheim). 1996 Dec;329(12):554-5. doi: 10.1002/ardp.19963291208.

3-Hydroxymethylphenytoin valproic acid ester (VAL-PHT) was designed as a new prodrug combining valproic acid and phenytoin, two anticonvulsant drugs with different pharmacological profiles. The compound was hydrolyzed by rat plasma esterases in vitro but exhibited only activity in the maximal electroshock seizure test (MES test) after intraperitoneal administration to mice. The compound did not protect against pentylenetetrazole-induced seizures. It is concluded that VAL-PHT acts as a prodrug displaying the anticonvulsant profile of phenytoin.