533-88-0

Basic information

• Product Name: 2-amino-5-hydroxyvaleric acid
• Synonyms: 2-amino-5-hydroxyvaleric acid;5-Hydroxy-2-aminovaleric acid;HAVA;2-azanyl-5-hydroxy-pentanoic acid;alpha-Amino-delta-hydroxy-n-valeric acid;alpha-Amino-delta-hydroxyvaleric acid;delta-Hydroxynorvaline;NSC 20896
• CAS NO: 533-88-0
• Molecular Formula: C₅H₁₁NO₃
• Molecular Weight: 133.15
• Mol File: 533-88-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: 218-220℃
• Boiling Point: 306.1 °C at 760 mmHg
• Flash Point: 138.9 °C
• Appearance: /
• Density: 1.241 g/cm³
• Vapor Pressure: 7.36E-05mmHg at 25°C
• Refractive Index: 1.504
• PKA: 2.51±0.24(Predicted)
• CAS DataBase Reference: 2-amino-5-hydroxyvaleric acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-5-hydroxyvaleric acid(533-88-0)
• EPA Substance Registry System: 2-amino-5-hydroxyvaleric acid(533-88-0)

Safety Data

• Hazardous Substances Data: 533-88-0(Hazardous Substances Data)

Usage

General Description

2-amino-5-hydroxyvaleric acid is a chemical compound with the formula C5H11NO3. It is also known as 5-hydroxynorvaline and is a non-proteinogenic amino acid. 2-amino-5-hydroxyvaleric acid has a hydroxyl group and an amino group on the carbon chain, giving it both hydrophilic and polar properties. 2-amino-5-hydroxyvaleric acid is found in certain plants and is considered to have potential therapeutic effects, including antioxidant and anti-inflammatory properties. It also has potential applications in the pharmaceutical and medical industries for developing new drugs and treatments.

InChI:InChI=1/C5H11NO3/c6-4(5(8)9)2-1-3-7/h4,7H,1-3,6H2,(H,8,9)

Synthetic route

2,3-dihydro-2H-furan (1191-99-7) → 2-amino-5-hydroxyvaleric acid (533-88-0)

Conditions	Yield
beim aufeinanderfolgenden Behandeln mit NaCN, wss.HCl und NH4Cl, mit wss.2CO3 und mit wss. Ba(OH)2;

4-butanolide (96-48-0) + oxalic acid diethyl ester (95-92-1) → 2-amino-5-hydroxyvaleric acid (533-88-0)

Conditions	Yield
With sulfuric acid und Hydrieren des Reaktionsprodukts an Raney-Nickel in wss.NH3;

glutamic acid 5-ethyl ester (45025-28-3) → 2-amino-5-hydroxyvaleric acid (533-88-0)

Conditions	Yield
With tetrahydrofuran; lithium borohydride

glutamic acid γ-methyl ester (1499-55-4) → 2-amino-5-hydroxyvaleric acid (533-88-0)

Conditions	Yield
Yield given. Multistep reaction;

δ-oxy-α-benzamino-n-valeric acid → 2-amino-5-hydroxyvaleric acid (533-88-0)

Conditions	Yield
With hydrogenchloride

1,3-dibromo-propane (109-64-8) + sodium compound of phthalimidomalonic acid ester → 2-amino-5-hydroxyvaleric acid (533-88-0)

Conditions	Yield
at 165 - 170℃; ueber mehreren Stufen;

hydrogenchloride (7647-01-0) + 2-benzoylamino-5-hydroxy-valeric acid (115938-76-6) → 2-amino-5-hydroxyvaleric acid (533-88-0)

sulfuric acid (7664-93-9) + 2-benzoylamino-5-hydroxy-valeric acid (115938-76-6) → 2-amino-5-hydroxyvaleric acid (533-88-0)

methanol (67-56-1) + 2-amino-5-hydroxyvaleric acid (533-88-0) → methyl 2-amino-5-hydroxyvalerate

Conditions	Yield
With sulfuric acid for 3h; Reflux;	90%

2-amino-5-hydroxyvaleric acid (533-88-0) → 5-hydroxy-2-(N'-phenyl-ureido)-valeric acid (860256-02-6)

Conditions	Yield
With sodium hydroxide anschliessendes Behandeln mit Phenylisocyanat;

potassium cyanate (590-28-3) + 2-amino-5-hydroxyvaleric acid (533-88-0) → 5-(3-hydroxy-propyl)-imidazolidine-2,4-dione

2-amino-5-hydroxyvaleric acid (533-88-0) → 5-hydroxy-2-oxo-pentanoic acid (104092-74-2)

Conditions	Yield
With kidneys-substances
durch Einwirkung von Nieren-Praeparaten unter aeroben Bedingungen;

2-amino-5-hydroxyvaleric acid (533-88-0) + 2,4-Dinitrofluorobenzene (70-34-8) → 3-(2,4-dinitro-anilino)-tetrahydro-pyran-2-one (22899-87-2)

Conditions	Yield
With ethanol; sodium hydrogencarbonate Ansaeuern des Reaktionsgemisches mit wss. Schwefelsaeure;

2-amino-5-hydroxyvaleric acid (533-88-0) + 2,4-Dinitrofluorobenzene (70-34-8) → 2-(2,4-dinitro-anilino)-5-hydroxy-valeric acid (108541-01-1)

Conditions	Yield
With ethanol; sodium hydrogencarbonate

2-amino-5-hydroxyvaleric acid (533-88-0) + benzoyl chloride (98-88-4) → 2-benzoylamino-5-hydroxy-valeric acid (115938-76-6)

Conditions	Yield
With alkali

2-amino-5-hydroxyvaleric acid (533-88-0) + benzoyl chloride (98-88-4) → 2-benzoylamino-5-benzoyloxy-valeric acid

Conditions	Yield
With alkali

2-amino-5-hydroxyvaleric acid (533-88-0) + chloroacetyl chloride (79-04-9) → 2-(2-chloro-acetylamino)-5-hydroxy-valeric acid

2-amino-5-hydroxyvaleric acid (533-88-0) + benzoyl chloride (98-88-4) → N,O-dibenzoyl-δ-oxy-α-amino-n-valeric acid

Conditions	Yield
in ganz schwach alkal.Loesung;

2-amino-5-hydroxyvaleric acid (533-88-0) + benzoyl chloride (98-88-4) → N-monobenzoyl-δ-oxy-α-amino-n-valeric acid

Conditions	Yield
in ausgepraegt alkal.Loesung;

2-amino-5-hydroxyvaleric acid (533-88-0) → pyrrolidine-α-carboxylic acid

Conditions	Yield
at 195 - 200℃;

hydrogenchloride (7647-01-0) + 2-amino-5-hydroxyvaleric acid (533-88-0) → pyrrolidine-α-carboxylic acid

2-amino-5-hydroxyvaleric acid (533-88-0) → 2-(2,4-dinitro-phenylhydrazono)-5-hydroxy-valeric acid (99864-61-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: durch Einwirkung von Nieren-Praeparaten unter aeroben Bedingungen View Scheme

2-amino-5-hydroxyvaleric acid (533-88-0) → 5-chloro-2-(2,4-dinitro-anilino)-valeric acid (117342-48-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous ethanol; NaHCO3 2: acetyl chloride; PCl5 View Scheme

2-amino-5-hydroxyvaleric acid (533-88-0) → 5-(3-hydroxy-propyl)-3-phenyl-imidazolidine-2,4-dione

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NaOH solution / anschliessendes Behandeln mit Phenylisocyanat 2: aqueous HCl View Scheme

2-amino-5-hydroxyvaleric acid (533-88-0) → Hexahydro-2-phenyl-1H-pyrrolo(1,2-c)imidazol-1,3-dione (2221-09-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. NaOH solution / anschliessendes Behandeln mit Phenylisocyanat 2: aqueous HCl 3: aqueous HBr<48percent > View Scheme

N-(tert-butyloxycarbonyl) azide (1070-19-5) + 2-amino-5-hydroxyvaleric acid (533-88-0) → 2-tert-Butoxycarbonylamino-5-hydroxy-pentanoic acid (85535-47-3)

2-amino-5-hydroxyvaleric acid (533-88-0) + benzyl bromide (100-39-0) → O-benzyl-5-hydroxynorvaline

Conditions	Yield
With hydrogenchloride In sodium hydroxide; water

2-amino-5-hydroxyvaleric acid (533-88-0) → 2-ethylamino-5-hydroxyvalerate methyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid / 3 h / Reflux 2: sodium hydride / N,N-dimethyl-formamide / 20 °C / Inert atmosphere View Scheme

2-amino-5-hydroxyvaleric acid (533-88-0) → methyl 5-bromo-2-ethylaminovalerate

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid / 3 h / Reflux 2: sodium hydride / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 3: bromine / tetrachloromethane / 2 h / 60 °C View Scheme

Upstream product

• 1191-99-7 2,3-dihydro-2H-furan 
• 7647-01-0 hydrogenchloride 
• 115938-76-6 2-benzoylamino-5-hydroxy-valeric acid 
• 7664-93-9 sulfuric acid 
• 109-64-8 1,3-dibromo-propane 
• 1499-55-4 glutamic acid γ-methyl ester 
• 45025-28-3 glutamic acid 5-ethyl ester 
• 96-48-0 4-butanolide 
• 95-92-1 oxalic acid diethyl ester 

Downstream Products

• 22899-87-2 3-(2,4-dinitro-anilino)-tetrahydro-pyran-2-one 
• 108541-01-1 2-(2,4-dinitro-anilino)-5-hydroxy-valeric acid 
• 115938-76-6 2-benzoylamino-5-hydroxy-valeric acid 
• 1224637-00-6 methyl 1-ethylpyrrolidine-2-carboxylate 
• 26116-12-1 1-ethyl-2-pyrrolidinemethanamine 
• 2221-09-2 Hexahydro-2-phenyl-1H-pyrrolo(1,2-c)imidazol-1,3-dione 
• 99864-61-6 2-(2,4-dinitro-phenylhydrazono)-5-hydroxy-valeric acid 
• 872782-23-5 5-(3-hydroxy-propyl)-imidazolidine-2,4-dione 
• 860256-02-6 5-hydroxy-2-(N'-phenyl-ureido)-valeric acid 

Relevant articles and documents

STRUCTURE OF CADYSTIN, THE UNIT-PEPTIDE OF CADMIUM-BINDING PEPTIDES INDUCED IN A FISSION YEAST, SCHIZOSACCHAROMYCES POMBE

The unit-peptide, cadystin, of cadmium-binding peptides occuring in a fission yeast, S. pombe was determined to have structure H-γ-Glu-Cys-γ-Glu-Cys-Cys-γGlu-Gly-OH; all Glu and two Cys being L-form, whereas one of the Cys's D-form.