70-26-8

Basic information

• Product Name: L-Ornithine
• Synonyms: (S)-2,5-Diaminovaleric acid;ORNITHINE;L-ORNITHINE;2,5-diaminopentanoic acid;(2S)-2,5-Diaminopentanoic acid;5-Amino-L-norvaline;Ornithine Phenylacetate
• CAS NO: 70-26-8
• Molecular Formula: C₅H₁₂N₂O₂
• Molecular Weight: 132.16
• EINECS: 200-731-7
• Product Categories: Amino Acids;Nutritional Supplements;Inhibitors
• Mol File: 70-26-8.mol
• Article Data: 61

Chemical Properties

• Melting Point: 140°C
• Boiling Point: 244.08°C (rough estimate)
• Flash Point: 140.508 °C
• Appearance: /
• Density: 1.1740 (rough estimate)
• Vapor Pressure: 1.08E-05mmHg at 25°C
• Refractive Index: 1.4496 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 1.705(at 25℃)
• CAS DataBase Reference: L-Ornithine(CAS DataBase Reference)
• NIST Chemistry Reference: L-Ornithine(70-26-8)
• EPA Substance Registry System: L-Ornithine(70-26-8)

Safety Data

• Hazardous Substances Data: 70-26-8(Hazardous Substances Data)

Usage

Chemical Properties

Crystals from alcoholether. Soluble in water and alcohol.

Uses

Different sources of media describe the Uses of 70-26-8 differently. You can refer to the following data:
1. Biochemical research; medicine.
2. hepatoprotectant, anticholesteremic

Definition

ChEBI: An optically active form of ornithine having L-configuration.

Synthesis Reference(s)

Canadian Journal of Chemistry, 31, p. 1060, 1953 DOI: 10.1139/v53-139

Purification Methods

Crystallise L-ornithine from water containing 1mM EDTA (to remove metal ions). [Perrin J Chem Soc 3125 1958, Rivard Biochemical Preparations 3 97 1955, Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 pp 2477-2491 1961, Beilstein 4 III 1346, 4 IV 2644.]

InChI:InChI=1/C5H12N2O2.C5H6O5/c6-3-1-2-4(7)5(8)9;6-3(5(9)10)1-2-4(7)8/h4H,1-3,6-7H2,(H,8,9);1-2H2,(H,7,8)(H,9,10)

Synthetic route

cyclo(-Orn(Boc)-L-Ala-) (126175-52-8) → L-ornithine (70-26-8)

Conditions	Yield
With hydrogenchloride at 110℃; for 24h;	62%

L-ornithine hydrochloride (3184-13-2) → L-ornithine (70-26-8)

Conditions	Yield
With calcium hydroxide In ethanol at 50℃; for 1.5h; Product distribution / selectivity;	43.95%
With acidic ion exchange resin (Marason C, H-type) In water Product distribution / selectivity;

glucose (50-99-7, 59-23-4, 921-60-8, 1949-88-8, 1990-29-0, 2152-76-3, 2595-97-3, 2595-98-4, 3458-28-4, 4205-23-6, 5934-56-5, 5978-95-0, 5987-68-8, 6027-89-0, 6038-51-3, 7635-11-2, 10030-80-5, 15572-79-9, 19163-87-2, 23567-25-1, 26566-61-0, 30077-17-9, 31103-86-3, 39665-52-6, 40866-07-7, 58367-01-4, 58407-05-9, 58407-06-0, 83198-69-0, 83198-70-3, 83198-71-4, 93780-23-5, 145920-48-5) → L-ornithine (70-26-8)

Conditions	Yield
mit Hilfe von Mutanten von Micrococcus glutamicus;

D-arginine (157-06-2) → L-ornithine (70-26-8) + urea (57-13-6)

Conditions	Yield
bei der Einw. von Leberpresssaft;
With barium dihydroxide
With arginase

L-arginine (74-79-3) → L-ornithine (70-26-8)

Conditions	Yield
With mammal liver
With barium dihydroxide
With urease; arginase

N2-(toluene-4-sulfonyl)-L-ornithine (19595-40-5) → L-ornithine (70-26-8)

Conditions	Yield
With hydrogen bromide; acetic acid

N-(toluene-4-sulfonyl)-L-glutamic acid-5-nitrile (42533-20-0) → L-ornithine (70-26-8)

Conditions	Yield
With methanol; ammonia; sodium
Multi-step reaction with 2 steps 1: platinum; acetic acid; aqueous HCl / Hydrogenation 2: HBr; acetic acid View Scheme

Sucrose (57-50-1) → L-ornithine (70-26-8)

Conditions	Yield
mit Hilfe von Mutanten von Micrococcus glutamicus;

(S)-2-Amino-5-[N'-((S)-2-amino-3-methyl-butyryl)-guanidino]-pentanoic acid; compound with oxalic acid → L-ornithine (70-26-8)

Conditions	Yield
With ammonium hydroxide

L-lysine (56-87-1) → L-alanin (56-41-7) + L-ornithine (70-26-8) + L-Aspartic acid (56-84-8) + glycine (56-40-6)

Conditions	Yield
With ammonium sulfate In water for 40h; Irradiation; Yield given. Further byproducts given. Yields of byproduct given;

L-lysine (56-87-1) → L-threonine (72-19-5) + L-ornithine (70-26-8) + L-Aspartic acid (56-84-8) + glycine (56-40-6)

Conditions	Yield
With ammonium sulfate In water for 40h; Irradiation; Yield given. Further byproducts given. Yields of byproduct given;
With trimagnesium phosphate In water for 40h; Irradiation; Yield given. Further byproducts given. Yields of byproduct given;

L-lysine (56-87-1) → L-ornithine (70-26-8) + L-Aspartic acid (56-84-8) + glycine (56-40-6) + 3-amino propanoic acid (107-95-9)

Conditions	Yield
With ammonium sulfate In water for 40h; Irradiation; Yield given. Further byproducts given. Yields of byproduct given;

L-arginine (74-79-3) → L-ornithine (70-26-8) + urea (57-13-6)

Conditions	Yield
With water; Montmorillonite at 25℃; Rate constant; Equilibrium constant; Mechanism;
With sodium azide; sodium dithionite; L-arginine amidinohydrolase from bacterium Bacillus subtilis; acetic acid; manganese(ll) chloride In water pH=9.5; Inert atmosphere; Enzymatic reaction;
With water; glycine Kinetics; Enzymatic reaction;
With recombinant Plasmodium falciparum arginase beginning at residue K22 bearing N-terminal histidine tag; water; manganese(ll) chloride at 37℃; for 8h; Kinetics; Reagent/catalyst; pH-value; aq. buffer; Enzymatic reaction;

Nα-acetyl-S-ornithine (6205-08-9) → L-ornithine (70-26-8)

Conditions	Yield
With Aspergillus oryzae acylase relative rates;

N5-acetyl-N5-hydroxy-L-ornithine (18928-01-3) → L-ornithine (70-26-8)

Conditions	Yield
With hydrogenchloride; hydrogen; palladium on activated charcoal 1.) reflux, 2 h; 2.) H2O, 25 deg C, 7 h; Multistep reaction;

2,2',ΔAla4,D-Ser4'>-GS (82155-99-5) → L-alanin (56-41-7) + L-valine (72-18-4) + D-Serine (312-84-5) + L-leucine (61-90-5) + L-ornithine (70-26-8) + L-proline (147-85-3)

Conditions	Yield
With hydrogen Product distribution;

C58H100N12O16 (82156-00-1) → L-alanin (56-41-7) + D-Serine (312-84-5) + L-leucine (61-90-5) + L-ornithine (70-26-8) + 2-oxo-propionic acid (127-17-3) + L-proline (147-85-3)

Conditions	Yield
With hydrogen Product distribution;

cyclo (-Gly-L-Orn-L-Val-3-amino-10-methyldodecanoyl-) → L-ornithine (70-26-8) + glycine (56-40-6) + (R)-3-((S)-2-Amino-3-methyl-butyrylamino)-10-methyl-dodecanoic acid

Conditions	Yield
With hydrogenchloride at 120℃; for 16h; Hydrolysis;	A n/a B n/a C 5.9 mg
With hydrogenchloride at 120℃; for 16h; Product distribution; Hydrolysis;

cyclo (-Gly-L-Orn-L-Ile-3-amino-10-methyldodecanoyl-) → L-isoleucine (73-32-5) + L-ornithine (70-26-8) + glycine (56-40-6) + 3-amino-10-methyldodecanoic acid

Conditions	Yield
With hydrogenchloride Product distribution; Hydrolysis;

N2-benzoyl-N5-benzoylcarbamoyl-L-ornithine benzoylamide → L-ornithine (70-26-8) + L-proline (147-85-3)

Conditions	Yield
With hydrogenchloride

Nδ-acetyl-L-ornithine (13215-18-4, 81397-94-6, 2185-16-2) + sulfuric acid (7664-93-9) → L-ornithine (70-26-8)

L-arginine (74-79-3) + aqueous Ba(OH)2 → L-ornithine (70-26-8)

Citrulline (372-75-8) + aqueous Ba(OH)2 → L-ornithine (70-26-8)

l(+)-arginine-hydrochloride → L-ornithine (70-26-8)

Conditions	Yield
With sulfuric acid

l(+)-arginine nitrate → L-ornithine (70-26-8)

Conditions	Yield
With barium dihydroxide Schuetteln mit Salicylaldehyd als Bariumsalz von Salicyliden-ornithin ab und hydrolysiert mit Salzsaeure oder Schwefelsaeure;

racemat → L-ornithine (70-26-8)

Conditions	Yield
With (-)-(R,R)-dibenzoyltartaric acid

α.δ-bis--n-valeric acid → 2-furanoic acid (88-14-2) + L-ornithine (70-26-8)

Conditions	Yield
With hydrogenchloride
With barium dihydroxide

ornithuric acid → L-ornithine (70-26-8) + benzoic acid (65-85-0)

Conditions	Yield
With hydrogenchloride

dl-arginine → L-ornithine (70-26-8) + urea, l-arginine

Conditions	Yield
bei der Einw. von Leberpresssaft;

L-ornithine (70-26-8) → δ-N-hydroxy-L-ornithine (35187-58-7, 40162-07-0, 40162-08-1, 93898-36-3)

Conditions	Yield
With β-nicotinamide adenine dinucleotide 2’-phosphate reduced tetrasodium salt; flavin-adenin dinucleotide, disodium salt at 25℃; for 12h; pH=8.0; TRIS buffer; Enzymatic reaction;	100%
With Rhizobium etli CFN42 ATCC51251 VbsO N-hydroxylase; flavin adenine dinucleotide; NADH at 25℃; pH=8; Kinetics; aq. buffer; Enzymatic reaction;
With Aspergillus fumigatus siderophore A at 25℃; for 0.166667h; pH=7.5; Enzymatic reaction;

L-ornithine (70-26-8) + di-tert-butyl dicarbonate (24424-99-5) → (S)-2,5-bis((tert-butoxycarbonyl)amino)pentanoic acid (57133-29-6)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water at 50℃; for 3h;	98%
With potassium carbonate

methanol (67-56-1) + L-ornithine (70-26-8) → L-ornithine methyl ester hydrochloride

Conditions	Yield
With hydrogenchloride	94%

L-ornithine (70-26-8) + diphenylborinic acid (2622-89-1) → C17H21BN2O2

Conditions	Yield
With sodium hydroxide for 4h; pH=8.5; Heating;	90%

L-ornithine (70-26-8) + benzyl chloroformate (501-53-1) → N-carboxybenzyl-L-ornithine (3304-51-6)

Conditions	Yield
Stage #1: L-ornithine With copper(II) carbonate In water for 0.5h; Stage #2: benzyl chloroformate With sodium hydroxide In water for 1h; Stage #3: With hydrogenchloride; ethylenediaminetetraacetic acid for 2h; Further stages.;	88%
Stage #1: L-ornithine With copper diacetate; sodium hydroxide In water Inert atmosphere; Stage #2: benzyl chloroformate With sodium hydroxide In dioxide; water Inert atmosphere; Stage #3: With ethylenediaminetetraacetic acid pH=4 - 5; Inert atmosphere;	73%
Stage #1: L-ornithine In water Substitution; complexation; Heating; Stage #2: benzyl chloroformate With sodium hydroxide In diethyl ether; water Acylation; Stage #3: With hydrogenchloride; hydrogen sulfide In diethyl ether; water Decomposition;	62%
Yield given. Multistep reaction;
Stage #1: L-ornithine With β‐cyclodextrin In aq. buffer at 20℃; for 5h; pH=8; Stage #2: benzyl chloroformate In aq. buffer at 20℃; Reagent/catalyst; chemoselective reaction;

L-ornithine (70-26-8) + 4-nitrophenyl palmitate (1492-30-4) → palmitoyl-(S)-ornithine (59012-45-2)

Conditions	Yield
With triethylamine In 1,4-dioxane; water at 50℃; for 4h;	86.5%

L-ornithine (70-26-8) + methyl chloroformate (79-22-1) → N,N-bis(methoxycarbonyl)-L-ornithine

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran at 20℃; Acylation;	86%

L-ornithine (70-26-8) → (S)-(-)-3-aminopiperidin-2-one (34294-79-6)

Conditions	Yield
Stage #1: L-ornithine With chloro-trimethyl-silane In methanol at 20℃; for 17h; Inert atmosphere; Stage #2: With sodium methylate In methanol at 0 - 20℃; for 2.5h;	86%
Multi-step reaction with 2 steps 1: HCl (g) / 1 h 2: NaOMe / methanol / 2 h View Scheme
With thionyl chloride In methanol at 20℃; for 0.5h;

L-ornithine (70-26-8) + 2,3-bis(acetyloxy)benzoyl chloride (65055-19-8) → N2,N5-bis(2,3-diacetoxybenzoyl)-L-ornithine (439152-11-1)

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran at 0 - 5℃; for 1h;	85%

L-ornithine (70-26-8) + 5-bromo-2,3-diacetoxybenzoyl chloride → N2,N5-bis(5-bromo-2,3-diacetoxybenzoyl)-L-ornithine

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran at 0 - 5℃; for 1h;	85%

L-ornithine (70-26-8) + dimethylsulfonium methyl sulfate → N-carboxybenzyl-L-ornithine (3304-51-6)

Conditions	Yield
With sodium hydroxide In water at 20℃; for 0.5h;	80%

L-ornithine (70-26-8) + (S)-5-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-aminopentanoic acid (147071-84-9) → H2N-L-Arg-L-Orn-OCH3

Conditions	Yield
Multistep reaction;	80%

L-ornithine (70-26-8) + water (7732-18-5) + copper(II) picrate (16049-03-9, 24264-11-7, 51209-41-7) → [Cu(L-ornithine)2(H2O)](picric acid)2

Conditions	Yield
at 50℃; for 1h;	80%

L-ornithine (70-26-8) + (fluorenylmethoxy)carbonyl chloride (28920-43-6) → Nα,Nε-bis(fluorenylmethoxycarbonyl)-L-ornithine (201046-59-5)

Conditions	Yield
	79%

L-ornithine (70-26-8) + N-ethoxycarbonylphthalimide (22509-74-6) → 2-amino-5-(1,3-dioxoisoindolin-2-yl)pentanoic acid hydrochloride salt

Conditions	Yield
Stage #1: L-ornithine; N-ethoxycarbonylphthalimide With copper(ll) sulfate pentahydrate; sodium hydrogencarbonate; sodium hydroxide In water at 20℃; for 3h; Stage #2: With hydrogenchloride In water at 20℃; for 1h;	77%

L-ornithine (70-26-8) + Boc-Phe-ONSu (3674-06-4) → (S)-2,5-Bis-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionylamino)-pentanoic acid (295321-41-4)

Conditions	Yield
With 4-methyl-morpholine In N,N-dimethyl-formamide at 20℃; for 8h; Acylation;	75%

(2S)-2-[4-(2-oxocyclopentan-1-ylmethyl)phenyl]propionic acid + L-ornithine (70-26-8) → S-loxoprofen ornithine salt

Conditions	Yield
In ethanol; water for 2h; Reflux;	74%

4-(((5bS,6aS,7aR,8R,8aS,9aS,9bS,10aS,10bS)-8a-isopropyl-10b-methyl-3-oxo-1,2,3,5,5b,6,6a,8,8a,9a,9b,10b-dodecahydrotris(oxireno)[2',3':4b,5;2'',3'':6,7;2''',3''':8a,9]phenanthro[1,2-c]furan-8-yl)oxy)-4-oxobutanoic acid (195883-06-8) + L-ornithine (70-26-8) → C29H38N2O10

Conditions	Yield
With 4-methyl-morpholine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In 1,4-dioxane; water at 20℃;	72%

copper(II) nitrate trihydrate + L-ornithine (70-26-8) + water (7732-18-5) + 1,10-phenanthroline hydrate (5144-89-8) → C18H21CuN4O5(1+)*NO3(1-)*2H2O

Conditions	Yield
Stage #1: copper(II) nitrate trihydrate; L-ornithine; water With sodium hydroxide Stage #2: 1,10-phenanthroline hydrate In ethanol at 60℃; for 6h;	70%

L-ornithine (70-26-8) + acrylonitrile (107-13-1) → Nα,N',Nα,N'-tetrakis(cyanoethyl)-L-ornithine (754170-66-6) + Nα,N',N'-tris(cyanoethyl)-L-ornithine

Conditions	Yield
Stage #1: L-ornithine; acrylonitrile With sodium hydroxide In tetrahydrofuran; water at 20℃; for 51h; Michael condensation; Reflux; Stage #2: With hydrogenchloride In tetrahydrofuran; water Cooling;	A 23.6% B 63.3%

L-ornithine (70-26-8) + formic acid ethyl ester (109-94-4) → N5-formyl-L-ornithine (5367-89-5)

Conditions	Yield
Stage #1: L-ornithine With water for 0.5h; Heating; Stage #2: formic acid ethyl ester With trifluoroacetic acid In methanol for 4h;	61%

L-ornithine (70-26-8) + diphenylborinic acid (2622-89-1) + acetic acid (64-19-7) → diphenyl[L-ornithinato-O,N]boron * AcOH

Conditions	Yield
In diethyl ether; ethanol; water for 2h; Heating;	60%
In ethanol; water refluxing ornithine with 15% excess of B-compd. (in EtOH/H2O=1:1, 2 h),filtration, washing (H2O), drying, recrystn. (EtOH/AcOH);	60%

L-ornithine (70-26-8) + trifluoroacetic anhydride (407-25-0) → 2,2,2-trifluoro-N-(3-(5-oxo-2-(trifluoromethyl)-2,5-dihydrooxazol-4-yl)propyl)acetamide (87341-12-6)

Conditions	Yield
at 0 - 60℃; for 2h;	55%
Yield given;

4-(chlorocarbonyl)pyridine (14254-57-0) + L-ornithine (70-26-8) → N2,N5-diisonicotinoyl-L-Orn

Conditions	Yield
With sodium hydroxide In water at -5℃; for 4h; pH:8-10;	52%

L-ornithine (70-26-8) + (2,3-dimethoxycarbonyloxy)benzoyl chloride (201296-89-1) → 2L,5-bis(8-methoxycarbonyloxy-3,4-dihydro-2,4-dioxo-1,3-benzoxazin-3-yl)-n-pentanoic acid

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran at 0 - 5℃; for 1h;	50%

L-ornithine (70-26-8) + diethyl phosphorochloridothioate (2524-04-1) → (S)-2-Amino-5-(diethoxy-thiophosphorylamino)-pentanoic acid

Conditions	Yield
With sodium hydroxide In ethanol for 2h;	47%

L-ornithine (70-26-8) + atorvastatin (134523-00-5) → (3R,5R)-7-[3-phenyl-4-[(phenylamino)carbonyl]-2-(4-fluorophenyl)-5-(1-methyl-ethyl)-pyrrol-1-yl]-3,5-dihydroxy-heptanoic acid L-ornithine salt

Conditions	Yield
In ethyl acetate	47%

5-amino-4,6-dichloropyridimine (5413-85-4) + L-ornithine (70-26-8) → (S)-2-Amino-5-(5-amino-6-chloro-pyrimidin-4-ylamino)-pentanoic acid (84856-36-0)

Conditions	Yield
With sodium hydroxide at 100℃; for 3h;	45%

Upstream product

• 542-32-5 (R,S)-2-aminoadipic acid 
• 5440-42-6 ethyl 2-acetamido-4-cyano-2-ethoxycarbonylbutanoate 
• 7438-77-9 Orn-δ-NOH 
• 2149-70-4 N-nitro-L-arginine 
• 7647-01-0 hydrogenchloride 
• 495-46-5 di(benzoyl)-L-(+)-ornithine 
• 65406-11-3 N²,N⁵-bis-phenylacetyl-ornithine 
• 1119-34-2 L-arginine hydrochloride 
• 7200-25-1 Arg 
• 74-79-3 L-arginine 
• 145876-67-1 N²,N⁵-bis-(furan-2-carbonyl)-ornithine 
• 69980-44-5 N⁵-benzoyl-DL-ornithine 
• 50-99-7 glucose 
• 157-06-2 D-arginine 

Downstream Products

• 5058-01-5 3-hydroxytetrahydro-2H-pyran-2-one 
• 2000-59-1 5-amino-2-oxo-valeric acid 
• 110-60-1 1,4-diaminobutane 
• 74-79-3 L-arginine 
• 70-26-8 2,5-diaminopentanoic acid 
• 455-61-8 N^α-Trifluoracetyl-L-ornithin 
• 5123-49-9 N⁵-trifluoroacetyl-L-ornithine 
• 372-75-8 Citrulline 
• 98-92-0 nicotinamide 
• 108477-92-5 di(p-nitrobenzoyl)-L-(+)-ornithine 
• 2274-58-0 (S)-2,5-bis-(benzyloxycarbonylamino)pentanoic acid 
• 5724-81-2 1-pyrroline 
• 7327-72-2 L-Orn-L-Asp-OH 
• 125790-77-4 (S)-2-Amino-5-{12-[12-(4-nitro-phenylamino)-dodecanoylamino]-dodecanoylamino}-pentanoic acid 

Relevant articles and documents

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