22430-23-5

Basic information

• Product Name: L-Mannono-1,4-lactone
• Synonyms: L-MANNONIC ACID GAMMA-LACTONE;L-MANNONIC GAMMA-LACTONE;L-MANNONO-1,4-LACTONE;L-MANNONO-GAMMA-LACTONE;L-MANNONOLACTONE;L-MANNONIC ACID-GAMMA-LACTONE CRYSTALLINE;l-mannonic γ-lactone;L-Mannonicacid-1,4-lactone
• CAS NO: 22430-23-5
• Molecular Formula: C₆H₁₀O₆
• Molecular Weight: 178.14
• EINECS: 228-678-5
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 22430-23-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 153-155 °C(lit.)
• Boiling Point: 467.9°Cat760mmHg
• Flash Point: 201.5°C
• Appearance: /
• Density: 1.766g/cm³
• Refractive Index: 1.625
• Storage Temp.: −20°C
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated), Water (Sparingly)
• PKA: 12.06±0.60(Predicted)
• CAS DataBase Reference: L-Mannono-1,4-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: L-Mannono-1,4-lactone(22430-23-5)
• EPA Substance Registry System: L-Mannono-1,4-lactone(22430-23-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 22430-23-5(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

L-mannono-1,4-lactone is a compound useful in organic synthesis.

InChI:InChI=1/C6H10O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2-5,7-10H,1H2/t2?,3?,4-,5+/m1/s1

Synthetic route

hydrogen cyanide (74-90-8) + L-arabinose (5328-37-0) → ethyl L-mannonate (152772-66-2) + L-mannono-1,4-lactone (22430-23-5)

Conditions	Yield
beim Behandeln des hesrgestellten Nitrils mit Bariumhydroxid in Wasser und Erwaermen des nach dem Ansaeuern erhaltenen Reaktionsprodukts mit Aethanol;

L-arabinose (5328-37-0) → L-mannono-1,4-lactone (22430-23-5)

Conditions	Yield
With barium dihydroxide; hydrogen cyanide; water Erhitzen des Reaktionsprodukts mit Butan-1-ol unter Eindampfen;
With barium dihydroxide; hydrogen cyanide; water Erhitzen des Reaktionsprodukts mit Aethanol unter Eindampfen;
Multi-step reaction with 2 steps 2: water / durch Eindampfen View Scheme

L-mannonic acid (133-42-6, 488-33-5, 526-95-4, 526-97-6, 576-36-3, 642-99-9, 1114-17-6, 3956-93-2, 6906-37-2, 7760-07-8, 13382-27-9, 20246-33-7, 20246-35-9, 20246-52-0, 20246-53-1, 21675-42-3, 22430-69-9, 24871-35-0, 28223-42-9, 28278-17-3, 51547-37-6) → L-mannono-1,4-lactone (22430-23-5)

Conditions	Yield
With water durch Eindampfen;

L-(+)-arabinose (87-72-9, 608-45-7, 608-46-8, 608-47-9, 2460-44-8, 6748-95-4, 6763-34-4, 7261-26-9, 7283-06-9, 7283-07-0, 7296-55-1, 7296-56-2, 7296-58-4, 7296-59-5, 7296-60-8, 7296-61-9, 7296-62-0, 7322-30-7, 10257-31-5, 10257-32-6, 10257-33-7, 10257-34-8, 10257-35-9, 19982-83-3, 20242-88-0, 28697-53-2, 36562-42-2, 41546-41-2, 89299-64-9, 107655-34-5, 115794-06-4, 115794-07-5, 130550-15-1, 130606-21-2) + ethanol (64-17-5) + sodium cyanide (143-33-9) → L-gluconic acid (157663-13-3) + ethyl L-mannonate (152772-66-2) + L-mannono-1,4-lactone (22430-23-5)

Conditions	Yield
With acetyl chloride 1) H2O, overnight, 2) r.t. to 5 deg C; Yield given. Multistep reaction;

L-(+)-arabinose (87-72-9, 608-45-7, 608-46-8, 608-47-9, 2460-44-8, 6748-95-4, 6763-34-4, 7261-26-9, 7283-06-9, 7283-07-0, 7296-55-1, 7296-56-2, 7296-58-4, 7296-59-5, 7296-60-8, 7296-61-9, 7296-62-0, 7322-30-7, 10257-31-5, 10257-32-6, 10257-33-7, 10257-34-8, 10257-35-9, 19982-83-3, 20242-88-0, 28697-53-2, 36562-42-2, 41546-41-2, 89299-64-9, 107655-34-5, 115794-06-4, 115794-07-5, 130550-15-1, 130606-21-2) + sodium cyanide (143-33-9) → ethyl L-mannonate (152772-66-2) + calcium L-gluconate (299-28-5, 3391-82-0, 4688-50-0, 6027-86-7, 6622-52-2, 14933-21-2, 18404-69-8, 45079-02-5, 69617-74-9, 71074-87-8, 90010-62-1, 121929-17-7) + L-mannono-1,4-lactone (22430-23-5)

Conditions	Yield
With ethanol; acetyl chloride 1) H2O, overnight, 2) r.t. to 5 deg C; Yield given. Multistep reaction;

2,3,5,6-tetra-O-acetyl-D-galactono-1,4-lactone (112241-17-5) → L-mannono-1,4-lactone (22430-23-5)

Conditions	Yield
With phosphate buffer; porcine pancreatic lipase for 7h;

D-sorbitol (50-70-4) → D-glucono-1,4-lactone (1198-69-2) + L-mannono-1,4-lactone (22430-23-5)

Conditions	Yield
With 1-Phenylbut-1-en-3-one; rhodium hydrido (PEt3)3 complex In N,N-dimethyl-formamide at 60 - 80℃; Yield given. Yields of byproduct given;

acetone (67-64-1) + L-mannono-1,4-lactone (22430-23-5) → 2,3,5,6-di-O-isopropylidene-D-gulono-1,4-lactone (67642-42-6)

Conditions	Yield
With toluene-4-sulfonic acid at 20℃; Inert atmosphere;	99%
With toluene-4-sulfonic acid In dimethoxypropane at 25℃; pH=3; Inert atmosphere;

L-mannono-1,4-lactone (22430-23-5) → D-glucitol (50-70-4)

Conditions	Yield
With Cu/Cr oxide; hydrogen In ethanol at 170 - 180℃; under 90007.2 Torr; for 10h;	95%

acetone (67-64-1) + L-mannono-1,4-lactone (22430-23-5) → (3aR,6S,6aR)-6-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one (49561-21-9)

Conditions	Yield
sulfuric acid; copper(II) sulfate for 22h;	94%
With sulfuric acid; copper(II) sulfate at 20℃; for 24h;	62%

2,2-dimethoxy-propane (77-76-9) + L-mannono-1,4-lactone (22430-23-5) → 1,2:3,4:5,6-tri-O-isopropylidene-L-mannitol (153059-35-9)

Conditions	Yield
Stage #1: L-mannono-1,4-lactone With lithium borohydride In methanol at 0℃; Inert atmosphere; Stage #2: 2,2-dimethoxy-propane With hydrogenchloride In 1,4-dioxane at 20℃; for 22h; Inert atmosphere;	87%

2,2-dimethoxy-propane (77-76-9) + L-mannono-1,4-lactone (22430-23-5) → (3aR,6S,6aR)-6-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one (49561-21-9)

Conditions	Yield
With toluene-4-sulfonic acid In acetone at 20℃; Inert atmosphere;	69%

cyclohexanone (108-94-1) + L-mannono-1,4-lactone (22430-23-5) → C18H26O6

Conditions	Yield
With sulfuric acid In toluene	65%

benzyl bromide (100-39-0) + L-mannono-1,4-lactone (22430-23-5) → (R)-3-Benzyloxy-5-((S)-1,2-dihydroxy-ethyl)-5H-furan-2-one (184766-06-1)

Conditions	Yield
With sodium hydride In dimethyl sulfoxide for 24h; Ambient temperature;	61%

L-mannono-1,4-lactone (22430-23-5) → L-mannaro-1,4:3,6-di-γ-lactone (214038-58-1)

Conditions	Yield
With nitric acid at 85℃; for 16h;	60%
With nitric acid	40%

tert-butyldimethylsilyl chloride (18162-48-6) + L-mannono-1,4-lactone (22430-23-5) → 3,6-Bis-O-(t-butyldimethylsilyl)-L-mannono-1,4-lacton (78283-79-1) + 2,6-Bis-O-(t-butyldimethylsilyl)-L-mannono-1,4-lacton (78283-99-5)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide for 12h; Ambient temperature;	A 33% B 56%

pivaloyl chloride (3282-30-2) + L-mannono-1,4-lactone (22430-23-5) → 2,5,6-tetra-O-pivaloyl-L-mannono-1,4-lactone + 2,3,5,6-tetra-O-pivaloyl-L-mannono-1,4-lactone

Conditions	Yield
With pyridine at 0℃; for 3h;	A 50% B 6.5%

L-mannono-1,4-lactone (22430-23-5) → (3S,4S)-3,4-dihydroxy-4-hexenoic acid-γ-lactone

Conditions	Yield
Stage #1: L-mannono-1,4-lactone With hydrogen bromide; acetic acid at 60℃; for 1h; Stage #2: With acetic acid; zinc for 3h;	50%
Stage #1: L-mannono-1,4-lactone With hydrogen bromide; acetic acid at 50℃; for 1h; Stage #2: With acetic acid; potassium hydroxide; zinc In water at -10 - 60℃; for 4h;	48%
Stage #1: L-mannono-1,4-lactone With hydrogen bromide; acetic acid at 50℃; for 1h; Stage #2: With zinc In water at -10 - 60℃;	48%

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) + L-mannono-1,4-lactone (22430-23-5) → 2,5-di-O-benzyl-L-mannaro-1,4:3,6-di-γ-lactone (213895-58-0)

Conditions	Yield
Stage #1: L-mannono-1,4-lactone With nitric acid In water Stage #2: O-benzyl 2,2,2-trichloroacetimidate With trifluorormethanesulfonic acid In 1,4-dioxane	37%

acetic anhydride (108-24-7) + L-mannono-1,4-lactone (22430-23-5) → 2,3,5,6-tetra-O-acetyl-D-galactono-1,4-lactone (112241-17-5)

Conditions	Yield
With zinc(II) chloride

L-mannono-1,4-lactone (22430-23-5) → L-mannonic acid amide (67008-28-0)

Conditions	Yield
With ammonia

L-mannono-1,4-lactone (22430-23-5) → mannaric acid-1=>4;6=>3-dilactone (826-91-5, 2900-01-8, 18404-59-6, 18404-63-2, 89772-72-5)

Conditions	Yield
With nitric acid at 50℃; γ.γ dilactone of/the/ l-manno-sugaroic acid;

dimethyl amine (124-40-3) + L-mannono-1,4-lactone (22430-23-5) → L-Mannonsaeure-dimethylamid

Conditions	Yield
In methanol

L-mannono-1,4-lactone (22430-23-5) → L-mannonic acid hydrazide (147598-40-1)

Conditions	Yield
With hydrazine In ethanol

L-mannono-1,4-lactone (22430-23-5) → L-mannitol (643-01-6)

Conditions	Yield
With lithium borohydride In methanol for 0.5h; Ambient temperature;

sulfuric acid (7664-93-9) + L-mannono-1,4-lactone (22430-23-5) + sodium amalgam → L-mannose (10030-80-5)

methanol (67-56-1) + ammonia (7664-41-7) + L-mannono-1,4-lactone (22430-23-5) → L-mannonic acid amide (67008-28-0)

hydrazine hydrate (7803-57-8) + L-mannono-1,4-lactone (22430-23-5) → L-mannonic acid hydrazide (147598-40-1)

Upstream product

• 74-90-8 hydrogen cyanide 
• 5328-37-0 L-arabinose 
• 133-42-6 L-mannonic acid 
• 87-72-9 L-(+)-arabinose 
• 64-17-5 ethanol 
• 143-33-9 sodium cyanide 
• 133-42-6 galactonic acid 
• 19242-59-2 D-galactose N,N'-diphenylformazan 
• 608-66-2 D-galactitol 
• 69-65-8 mannitol 
• 50-70-4 D-sorbitol 
• 112241-17-5 2,3,5,6-tetra-O-acetyl-D-galactono-1,4-lactone 

Downstream Products

• 643-01-6 L-mannitol 
• 10030-80-5 L-mannose 
• 50-99-7 galactose 
• 133-42-6 gluconic acid 
• 918899-62-4 l-manno-sugaroic acid 
• 1426415-10-2 (3S,4R,6S)-3,4-O-isopropylidene-6-(3,5-dinitrobenzoyloxymethyl)tetrahydro-2H-pyran-3,4-diol 
• 1426415-12-4 (3S,4R,6S)-3,4-O-isopropylidene-6-(tosyloxymethyl)tetrahydro-2H-pyran-3,4-diol 
• 596103-06-9 ((3aS,4R,6aR)-2,2- dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)methanol 
• 213895-58-0 2,5-di-O-benzyl-L-mannaro-1,4:3,6-di-γ-lactone 
• 3118-85-2 DL-mannonic acid amide 
• 121570-26-1 1-(3-chlorophenyl)-3-(1,2,3-tri-O-acetyl-L-threo-glycerol-1-yl)-4,5-pyrazoledione 4-(3-chlorophenylhydrazone) 
• 89912-70-9 5-O-acetyl-3,6-anhydro-3-C-(3-chlorophenylazo)-L-xylo-2-hexulosono-1,4-lactone 2-(3-chlorophenylhydrazone) 
• 89912-64-1 L-threo-2,3-hexodiulosono-1,4-lactone 2,3-bis(3-chlorophenylhydrazone) 
• 89912-69-6 3,6-anhydro-3-C-(3-chlorophenylazo)-L-xylo-2-hexulosono-1,4-lactone 2-(3-chlorophenylhydrazone) 

Relevant articles and documents

A new efficient access to glycono-1,4-lactones by oxidation of unprotected itols by catalytic hydrogen transfer with RhH(PPh3)4-benzalacetone system

Treatment of unprotected pentitols and hexitols with RhH(PPh3)4-benzalacetone system leads exclusively to glycono-1,4-lactones in 60-96% yield.

Deoxyiminoalditols from aldonolactones; I. Preparation of 1,4-dideoxy-1,4-iminohexitols with D- and L-allo and D- and L-talo configuration: Potential glycosidase inhibitors

1,4-Dideoxy-1,4-iminohexitols were prepared by a convenient two-step reaction from 2,6-dibromo-2,6-dideoxyhexono-1,4-lactones by treatment with aqueous ammonia and subsequent reduction of the carboxy function with sodium borohydride. By interchange of the reactions, the dibromolactones were reduced to 2,6-dibromohexitols, which by reaction with aqueous ammonia yielded the same imino compounds. Thus, from 2,6-dibromo-2,6-dideoxy-D-mannono- (1) and -D-glucono-1,4-lactone (9) the 1,4-dideoxy-1,4-imino-L-allitol (6) and -D-talitol (14) were prepared, respectively. These two compounds were also obtained from 2,6-dibromo-2,6-dideoxy-D-mannitol (5) and -D-glucitol (13), respectively, by reaction with aqueous ammonia. The enantiomeric 1,4-dideoxy-1,4-imino-D-allitol (18) and -L-talitol (22) were prepared similarly from the new 2,6-dibromo-2,6-dideoxy-L-mannono- (16) and -L-glucono-1,4-lactone (20), via the dibromo-L-hexitols 17 and 21, respectively. The ring closure of the dibromo compounds with ammonia has been shown to proceed via epoxides.