58-56-0

Basic information

• Product Name: Pyridoxine hydrochloride
• Synonyms: campoviton6;hexabetalin;hexa-betalin(r);hexabionehydrochloride;hexavibex;hexermin;hexobion;paxadon
• CAS NO: 58-56-0
• Molecular Formula: C₈H₁₂NO₃*Cl
• Molecular Weight: 205.64
• EINECS: 200-386-2
• Product Categories: Biochemistry;Pyridinium Compounds;Vitamins;Nutritional Supplements;Vitamins and derivatives;Aromatics;Heterocycles;Vitamin Ingredients;Vitamin series;Isolabel;vitamin;Inhibitors
• Mol File: 58-56-0.mol

Chemical Properties

• Melting Point: 214-215 °C(lit.)
• Boiling Point: 491.9 °C at 760 mmHg
• Flash Point: 9℃
• Appearance: White to almost white/Crystalline Powder
• Density: 1.2784 (rough estimate)
• Vapor Density: 7.1 (vs air)
• Refractive Index: 1.5800 (estimate)
• Storage Temp.: 2-8°C
• Solubility: H2O: 0.1 g/mL at 20 °C, clear, colorless
• Water Solubility: 0.1 g/mL (20 ºC)
• Sensitive: Light Sensitive
• Stability: Stable. Protect from air and light.
• Merck: 14,7982
• BRN: 3632435
• CAS DataBase Reference: Pyridoxine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridoxine hydrochloride(58-56-0)
• EPA Substance Registry System: Pyridoxine hydrochloride(58-56-0)

Safety Data

• Hazard Codes: Xi,T,F
• Statements: 36/37/38-39/23/24/25-23/24/25-11
• Safety Statements: 26-37/39-45-36/37-16-7-24/25
• RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution
• WGK Germany: 2
• RTECS: UV1350000
• F: 8-10
• TSCA: Yes
• Hazardous Substances Data: 58-56-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Pyridoxine hydrochloride is used as a supplement for the prevention and treatment of vitamin B6 deficiency. It is essential for the proper functioning of the nervous system, the synthesis of neurotransmitters, and the metabolism of amino acids.
Used in Food Industry:
Pyridoxine hydrochloride is used as a nutrient additive in the food industry to fortify various food products, ensuring an adequate intake of vitamin B6 for consumers.
Used in Cosmetic Industry:
Pyridoxine hydrochloride is used in the cosmetic industry as an ingredient in skincare products, where it helps promote skin health and maintain a youthful appearance.
Used in Research:
Pyridoxine hydrochloride is used in scientific research as a component of the B6 complex, which is involved in various cellular processes and can be studied for its effects on different biological systems.
Brand Name:
Hexa-Betalin (Lilly) is a brand name for pyridoxine hydrochloride, which is used as a supplement to treat vitamin B6 deficiency and related conditions.

Nutrition supplements

Pyridoxine hydrochloride is the hydrochloride salt of Vitamin B6. Vitamin B6 (B6) is a water-soluble vitamin, which can be found in various foods such as fish, poultry, whole grains, legumes, banana, nuts, and sesame.Vitamin B6 has an important role in the metabolism of amino acids as a coenzyme, pyridoxal 5'-phosphate.? B6 may exert an anticolon tumor effect by the protection of the colon epithelium from damage in rats treated with 1,2-dimethylhidrazine (DMH) and to decreased lithocholic acid, a colon carcinogen. Vitamin B6 may prevent such diseases by lowering inflammation.

Biochem/physiol Actions

Vitamin B6 is an essential coenzyme for amino acid, carbohydrate and lipid metabolism. Pyridoxine serves as a primary source in multivitamins. Pyridoxine deficiency is associated with peripheral neuropathy.

Clinical Use

Vitamin B6

Safety Profile

Poison by intravenous route. Moderately toxic by ingestion, intramuscular, and subcutaneous routes. Human reproductive effects by ingestion and intramuscular routes: postpartum changes. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and HCl.

Drug interactions

Potentially hazardous interactions with other drugs None known

Metabolism

Pyridoxine is metabolised to its active form pyridoxamine phosphate. It is stored mainly in the liver where there is oxidation to 4-pyridoxic acid and other inactive metabolites which are excreted in the urine.

Purification Methods

Purify the vitamin by recrystallisation from EtOH/Me2CO, n-BuOH or MeOH/Et2O. Its solubility in H2O is 22%, and in EtOH it is 1.1%. It is insoluble in Et2O and CHCl3. Acidic aqueous solutions are stable at 120o/30minute. The free base has m 159-160o after recrystallisation from Me2CO and sublimation at 140-145o/0.0001mm. It has UV max at 290nm ( 84,000), 253 and 325nm ( 3,700 and 7,100) in 0.1N aqueous HCl. [Khua & Wendt Chem Ber 71 780 1938, 72 311 1939, Harris & Folkers J Am Chem Soc 61 1242 1939, Harris et al. J Am Chem Soc 62 3198 1940, Beilstein 21/5 V 492.]

InChI:InChI=1/C8H11NO3.ClH/c1-5-8(12)7(4-11)6(3-10)2-9-5;/h2,10-12H,3-4H2,1H3;1H/p-1

Synthetic route

pyridoxine triacetate (10030-93-0) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
With hydrogenchloride In water for 2h; Heating;	98%
With hydrogenchloride; water for 2h; Heating / reflux;	72%

5-hydroxy-6-methylpyridine-3,4-dicarboxylic acid diethyl ester (2397-71-9) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
Stage #1: 5-hydroxy-6-methylpyridine-3,4-dicarboxylic acid diethyl ester With sodium tetrahydroborate; iron(II) sulfate; N,N-dimethyl-aniline In tetrahydrofuran for 4h; Reflux; Stage #2: With hydrogenchloride In tetrahydrofuran at 20℃; Reagent/catalyst; Solvent;	93.4%

4,5-dihydroxymethyl-2-methyl-2-cyclopentenone → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
Stage #1: 4,5-dihydroxymethyl-2-methyl-2-cyclopentenone With ozone In methanol; water at -30℃; for 3h; Stage #2: With ammonia In methanol; water at 20 - 25℃; for 3h; Stage #3: With hydrogenchloride; pyrographite In ethanol at 55 - 60℃; for 1h; Temperature; Solvent;	92%

2-hydroxymethyl-3-cyano-4-hydroxy-n-butyraldehyde + methyl 2-aminopropanoate monohydrochloride (13515-97-4) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
Stage #1: 2-hydroxymethyl-3-cyano-4-hydroxy-n-butyraldehyde; methyl 2-aminopropanoate monohydrochloride With sodium methylate In methanol at 30 - 50℃; for 5h; Green chemistry; Stage #2: With hydrogenchloride In methanol; water for 2h; Temperature; Solvent; Reagent/catalyst; Reflux; Green chemistry;	90.5%

4-methyl-5-dimethyl-tert-butylsiloxyoxazole + 2-propyl-4,7-dihydro-2H-1,3-dioxepine (4469-34-5) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
Stage #1: 4-methyl-5-dimethyl-tert-butylsiloxyoxazole; 2-propyl-4,7-dihydro-2H-1,3-dioxepine at 115 - 120℃; for 10h; Stage #2: With water In ethanol at 20℃; for 3h; Stage #3: With hydrogenchloride In ethanol; water at 20℃; for 2h;	89.5%

Diels-Alder adduct (5205-63-0) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
Stage #1: Diels-Alder adduct With hydrogenchloride In ethanol; water at 20℃; for 2h; Stage #2: In ethanol; water for 2h;	86.05%

C8H13NO4 → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
With hydrogenchloride; pyrographite In ethanol; water at 75 - 78℃; for 3h; Temperature;	83.5%

4-methyl-5-triisopropylsiloxyoxazole + 2-propyl-4,7-dihydro-2H-1,3-dioxepine (4469-34-5) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
Stage #1: 4-methyl-5-triisopropylsiloxyoxazole; 2-propyl-4,7-dihydro-2H-1,3-dioxepine at 115 - 120℃; for 10h; Stage #2: With water In ethanol at 20℃; for 3h; Stage #3: With hydrogenchloride In ethanol; water at 20℃; for 2h;	82.7%

2-propyl-4,7-dihydro-2H-1,3-dioxepine (4469-34-5) + 4-methyl-5-butoxy1,3-oxazole (24201-52-3) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
Stage #1: 2-propyl-4,7-dihydro-2H-1,3-dioxepine; 4-methyl-5-butoxy1,3-oxazole With calcium oxide at 150℃; for 12h; Diels-Alder Cycloaddition; Stage #2: With hydrogenchloride In ethanol; water at 20 - 60℃; for 12h; Stage #3: With hydrogenchloride In water for 1h; pH=8; Reagent/catalyst; Reflux;	80%

5-ethoxy-4-methyl-oxazole (5006-20-2) + 2-propyl-4,7-dihydro-2H-1,3-dioxepine (4469-34-5) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
With hydrogenchloride Diels-Alder Cycloaddition;	78.5%

3-amino-4,5-bis(aminomethyl)2-methylpyridine trihydrochloride (90330-16-8) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
With sulfuric acid; sodium nitrite In water at 90℃; for 2h;	75%

2-Methyl-3-hydroxy-4,5-bis-(bromomethyl)-pyridine hydrobromide (39984-49-1) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
With water; silver(I) chloride for 0.333333h; Heating;	68%
Multi-step reaction with 2 steps 1: 2.) AcONa / 1.) DMF, 55 degC, 1 h; 2.) DMF, 85 degC, 2.5 h 2: 98 percent / 2N HCl / H2O / 2 h / Heating View Scheme

pyridoxamine dihydrochloride (524-36-7) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
With sulfuric acid; water; sodium nitrite at 20 - 90℃; for 2h;	25%

Thiamine hydrochloride (67-03-8) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
With N-Bs In isopropyl alcohol at 25℃; for 0.5h;

L-1-Deoxy<1,1,1-(2)H3,(RS)-5-(2)H1>xylulose (80095-36-9) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
With D-glucose; Escherichia coli B WG2 Mechanism;

3-amino-4-aminomethyl-5-hydroxymethyl-2-methylpyridine dihydrochloride (83537-53-5) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
With cis-nitrous acid In water at 90℃;

Acetic acid 4-acetoxymethyl-2,5-dimethoxy-2-(1-methoxycarbonylamino-ethyl)-2,5-dihydro-furan-3-ylmethyl ester → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
With hydrogenchloride In water Yield given;

hydrogenchloride (7647-01-0) + 4,5-bis-aminomethyl-2-methyl-pyridin-3-ol (45996-87-0) + aqueous NaNO2 → pyridoxal hydrochloride (58-56-0) + <5-chloromethyl>-3-hydroxy-2-methyl-<4>pyridyl>-methanol

hydrogenchloride (7647-01-0) + 4-ethoxymethyl-5-hydroxymethyl-2-methyl-pyridin-3-ol; hydrochloride → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
at 155 - 160℃;

5-amino-6-methylpyridine-3,4-dicarbonitrile (71058-42-9) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / conc. HCl, H2 / 5 percent Pd-C / methanol; H2O / 3.5 h / Ambient temperature 2: 75 percent / sodium nitrite, H2SO4 / H2O / 2 h / 90 °C View Scheme

5-acetoxymethyl-3-amino-2-methylpyridine-4-carbonitrile (83537-57-9) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 88 percent / 1) conc. HCl, H2; 2) 0.2 N HCl / 1) 5 percent Pd-C / methanol; H2O / 1) 1 h, RT; 2) 1 h, 80 deg C 2: nitrous acid / H2O / 90 °C View Scheme

3,4-bis(hydroxymethyl)furan (14496-24-3) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: 100 percent / pyridine 2: 57 percent / p-toluenesulfonic acid / 2 h / 0 - 5 °C 3: electrochemical oxidation 4: HCl / H2O View Scheme

3,4-furan dimethanol diacetate (30614-73-4) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 57 percent / p-toluenesulfonic acid / 2 h / 0 - 5 °C 2: electrochemical oxidation 3: HCl / H2O View Scheme

Acetic acid 4-acetoxymethyl-2-(1-methoxycarbonylamino-ethyl)-furan-3-ylmethyl ester (79588-15-1) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: electrochemical oxidation 2: HCl / H2O View Scheme

1,3-dihydro-6-methyl-7-iodofuro(3,4-c)pyridine (104307-94-0) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 36 percent / Na, MeOH / CuI2 / various solvent(s) / 16 h / Heating 2: 78 percent / 48percent HBr / 2 h / Heating 3: 68 percent / H2O, AgCl / 0.33 h / Heating View Scheme

1,3-dihydro-6-methyl-7-methoxyfuro(3,4-c)pyridine (104307-95-1) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / 48percent HBr / 2 h / Heating 2: 68 percent / H2O, AgCl / 0.33 h / Heating View Scheme

1,3-dihydro-6-methyl-7-trimethylstannylfuro(3,4-c)pyridine (104307-93-9) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: 99 percent / I2 / CHCl3 / 18 h / Ambient temperature 2: 36 percent / Na, MeOH / CuI2 / various solvent(s) / 16 h / Heating 3: 78 percent / 48percent HBr / 2 h / Heating 4: 68 percent / H2O, AgCl / 0.33 h / Heating View Scheme

4,5'-O-isobutylidenepyridoxine (1622-67-9) → pyridoxal hydrochloride (58-56-0)

Conditions	Yield
With hydrogenchloride; water under 300.03 Torr; for 2h; Product distribution / selectivity; Heating / reflux;
Stage #1: 4,5'-O-isobutylidenepyridoxine With hydrogenchloride; water In tetrahydrofuran at 60 - 120℃; under 150.015 Torr; for 3h; Stage #2: With pyrographite In water at 0 - 60℃; Product distribution / selectivity;

3-isopropyl-1,5-dihydro[1,3]dioxepino-3-methyl-4-n-butoxy-7-oxa-2-azabicyclo[2.2.1]hept-2-ene (717916-87-5) → pyridoxal hydrochloride (58-56-0) + 4,5'-O-isobutylidenepyridoxine (1622-67-9)

Conditions	Yield
Stage #1: 3-isopropyl-1,5-dihydro[1,3]dioxepino-3-methyl-4-n-butoxy-7-oxa-2-azabicyclo[2.2.1]hept-2-ene With water; acetic acid In tetrahydrofuran at 60℃; under 760.051 Torr; for 4h; Stage #2: With hydrogenchloride; water In tetrahydrofuran at 0 - 60℃; for 5h; Product distribution / selectivity;
Stage #1: 3-isopropyl-1,5-dihydro[1,3]dioxepino-3-methyl-4-n-butoxy-7-oxa-2-azabicyclo[2.2.1]hept-2-ene With water In tetrahydrofuran at 60℃; under 760.051 Torr; for 4h; Stage #2: With hydrogenchloride In tetrahydrofuran at 20 - 60℃; for 5h; Product distribution / selectivity;

concentrated H2 SO4 + pyridoxal hydrochloride (58-56-0) → isopropylidene pyridoxine

Conditions	Yield
In acetone	100%

pyridoxal hydrochloride (58-56-0) → 4,5-bis(chloromethyl)-3-hydroxy-2-methylpyridinium chloride (39984-50-4)

Conditions	Yield
With thionyl chloride In N,N-dimethyl-formamide for 0.5h; Reflux; Inert atmosphere;	99%
With thionyl chloride In dichloromethane; N,N-dimethyl-formamide for 12h; Reflux;	96%
With thionyl chloride; N,N-dimethyl-formamide at 80℃; for 3h;	93%

pyridoxal hydrochloride (58-56-0) + 4-aminobenzene sulfonic acid (121-57-3) → C14H14N2O5S (1122445-21-9)

Conditions	Yield
Stage #1: pyridoxal hydrochloride With RuCl2(PPh3)2(BAOBEA); dihydrogen peroxide In water at 60℃; for 0.25h; Stage #2: 4-aminobenzene sulfonic acid In water for 0.0833333h; Reflux;	98.25%

pyridoxal hydrochloride (58-56-0) + 2,2-dimethoxy-propane (77-76-9) → (2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methanol (1136-52-3)

Conditions	Yield
With toluene-4-sulfonic acid In acetone at 20℃;	98%
With toluene-4-sulfonic acid In acetone at 20℃; for 23h;	96%
With toluene-4-sulfonic acid In acetone at 20℃; for 23h;	96%
With toluene-4-sulfonic acid In acetone at 20℃; for 20h; Inert atmosphere;	86%
With toluene-4-sulfonic acid In water; acetone for 20h; Inert atmosphere;	80%

pyridoxal hydrochloride (58-56-0) + acetic anhydride (108-24-7) → pyridoxine triacetate (10030-93-0)

Conditions	Yield
With triethylamine In tert-butyl methyl ether at 50 - 65℃; for 2.5h; Industry scale; Heating / reflux;	96%
With pyridine Ambient temperature;	57%
With pyridine

pyridoxal hydrochloride (58-56-0) + acetic anhydride (108-24-7) → 2,4-dimethyl-5-acetoxymethylpyridin-3-ol (53580-75-9)

Conditions	Yield
With zinc for 2h; Reflux;	95%

cobalt(II) chloride hexahydrate + Glutamic acid (617-65-2) + pyridoxal hydrochloride (58-56-0) → Co(2+)*C5HN(CH3)(O)(CH2OH)2(1-)*OOCCH2CH2(NH2)CHCOO(2-)*H(1+)*3H2O=Co{C5HN(CH3)(O)(CH2OH)2}(C5H8NO4)*3H2O

Conditions	Yield
With lithium carbonate In water byproducts: CO2; to soln. pyridoxine/water was added equimolar amt. glutamic acid and excess Li2CO3, after evolution CO2 completed addn. equimolar soln. CoCl2/H2O, formation of pink ppt.; ppt. separated, washed (EtOH and ether) until powdery, elem. anal.;	94.4%

pyridoxal hydrochloride (58-56-0) → 3-hydroxy-5-hydroxymethyl-2,4-dimethylpyridinium chloride (148-51-6)

Conditions	Yield
Stage #1: pyridoxal hydrochloride With acetic acid; zinc for 12h; Reflux; Stage #2: With hydrogenchloride In methanol at 0℃; for 2h;	94%
Stage #1: pyridoxal hydrochloride With acetic acid; zinc for 12h; Reflux; Stage #2: With hydrogenchloride In methanol; water at 0℃; for 2h;	94%
With acetic acid; zinc for 24h; Reflux;	94%
Stage #1: pyridoxal hydrochloride With acetic acid; zinc at 120℃; for 3h; Stage #2: With hydrogenchloride In methanol at 60℃; for 1h;	93%
Multi-step reaction with 2 steps 1: zinc / 72 h / Reflux 2: hydrogenchloride / water / 8 h / 50 °C View Scheme

pyridoxal hydrochloride (58-56-0) → 4,5-bis-chloromethyl-2-methyl-pyridin-3-ol (102694-13-3)

Conditions	Yield
With thionyl chloride In N,N-dimethyl-formamide for 0.5h; Reflux;	93%
With thionyl chloride In N,N-dimethyl-formamide for 0.5h; Inert atmosphere; Reflux;	93%

pyridoxal hydrochloride (58-56-0) + 2,2-dimethoxy-propane (77-76-9) → (2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methanol (1136-52-3) + 1,5-dihydro-3,3,8-trimethyl<1,3>dioxepino<5,6-y>pyridin-9-ol (948-00-5)

Conditions	Yield
With sulfuric acid In dichloromethane for 6h; Heating;	A 92% B n/a

pyridoxal hydrochloride (58-56-0) → 1,5-dihydro-3,3,8-trimethyl<1,3>dioxepino<5,6-y>pyridin-9-ol (948-00-5) + 2,2-dimethoxy-propane (77-76-9)

Conditions	Yield
With sulfuric acid In dichloromethane for 6h; Heating; Title compound not separated from byproducts;	A n/a B 92%

pyridoxal hydrochloride (58-56-0) + acetone (67-64-1) → (2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methanol hydrochloride (6953-28-2)

Conditions	Yield
With hydrogenchloride	92%
With hydrogenchloride for 2.5h;	90.9%
With hydrogenchloride at 20 - 30℃; for 6h;	85%
With hydrogenchloride HCl introduction below 10 degC, then -10 degC, overnight;	54%
With hydrogenchloride at 0℃; for 2h;	27.3 g

pyridoxal hydrochloride (58-56-0) + acetone (67-64-1) → (2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methanol (1136-52-3)

Conditions	Yield
With thionyl chloride In chloroform at 20℃; for 6h; ketalization;	91%
With sulfuric acid at 20℃;	65%
With Dess-Martin periodane; toluene-4-sulfonic acid at 20℃; for 20h; Inert atmosphere;	63%

pyridoxal hydrochloride (58-56-0) + cyclohexanone (108-94-1) → 3,4'-O-cyclohexylidenepyridoxine (4632-05-7)

Conditions	Yield
With thionyl chloride In chloroform at 20℃; ketalization;	90%
With sulfuric acid
Acidic conditions;

pyridoxal hydrochloride (58-56-0) + acetone (67-64-1) → 1,5-dihydro-3,3,8-trimethyl<1,3>dioxepino<5,6-y>pyridin-9-ol (948-00-5)

Conditions	Yield
With thionyl chloride In chloroform at 0 - 20℃; for 7h; ketalization;	90%
With hydrogenchloride at 3 - 20℃;	87%
(i) HCl, (ii) aq. K2CO3; Multistep reaction;

pyridoxal hydrochloride (58-56-0) + acetone (67-64-1) → chlorhydrate d'hydroxy-8 trimethyl-2,2,7 pyrido-<4,5-e>dioxa 1,3-cycloheptane (111422-99-2)

Conditions	Yield
With hydrogenchloride at 0℃; for 1h;	88%

Decan-2-one (693-54-9) + pyridoxal hydrochloride (58-56-0) → 5-(hydroxymethyl)-2,8-dimethyl-2-octyl-4H-[1,3]dioxino[4,5-c]pyridine

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 17h; Reflux; Dean-Stark;	87%

pyridoxal hydrochloride (58-56-0) + benzoic acid hydrazide (613-94-5) → N'-{(3-hydroxyl-5-(hydroxymethyl)-2-methylpyridin-4-yl)methylene}benzohydrazide hydrochloride

Conditions	Yield
Stage #1: pyridoxal hydrochloride With manganese(IV) oxide; sulfuric acid In water at 60 - 70℃; Stage #2: benzoic acid hydrazide In water for 0.166667h; Heating;	86%

4,4'-dimethoxytrityl chloride (40615-36-9) + pyridoxal hydrochloride (58-56-0) → C50H47NO7

Conditions	Yield
In pyridine; dichloromethane at 20℃; Inert atmosphere;	85%

pyridoxal hydrochloride (58-56-0) + tert-butylchlorodiphenylsilane (58479-61-1) → C40H47NO3Si2

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	83%
With triethylamine In tetrahydrofuran for 1.5h; Cooling with ice;	67%

pyridoxal hydrochloride (58-56-0) + benzyl bromide (100-39-0) → [5-(benzyloxy)-4-(hydroxymethyl)-6-methylpyridin-3-yl]methanol (7442-21-9)

Conditions	Yield
Stage #1: pyridoxal hydrochloride With potassium carbonate In acetonitrile at 90℃; for 1h; Stage #2: benzyl bromide In acetonitrile for 3h; Reflux;	83%

Upstream product

• 10030-93-0 pyridoxine triacetate 
• 90330-16-8 3-amino-4,5-bis(aminomethyl)2-methylpyridine trihydrochloride 
• 39984-49-1 2-Methyl-3-hydroxy-4,5-bis-(bromomethyl)-pyridine hydrobromide 
• 67-03-8 Thiamine hydrochloride 
• 80095-36-9 L-1-Deoxy<1,1,1-(2)H3,(RS)-5-(2)H1>xylulose 
• 83537-53-5 3-amino-4-aminomethyl-5-hydroxymethyl-2-methylpyridine dihydrochloride 
• 7647-01-0 hydrogenchloride 
• 45996-87-0 4,5-bis-aminomethyl-2-methyl-pyridin-3-ol 
• 71058-42-9 5-amino-6-methylpyridine-3,4-dicarbonitrile 
• 83537-57-9 5-acetoxymethyl-3-amino-2-methylpyridine-4-carbonitrile 
• 14496-24-3 3,4-bis(hydroxymethyl)furan 
• 30614-73-4 3,4-furan-dimethanol diacetate 
• 79588-15-1 Acetic acid 4-acetoxymethyl-2-(1-methoxycarbonylamino-ethyl)-furan-3-ylmethyl ester 
• 104307-94-0 1,3-dihydro-6-methyl-7-iodofuro(3,4-c)pyridine 

Downstream Products

• 633-72-7 4,5-bis-hydroxymethyl-3-methoxy-2-methyl-pyridine 
• 3131-27-9 3-Hydroxy-5-hydroxymethyl-4-methoxymethyl-2-methylpyridine hydrochloride 
• 447-05-2 5-hydroxy-4-(hydroxymethyl)-6-methyl-3-pyridylmethyl dihydrogen phosphate 
• 10030-93-0 pyridoxine triacetate 
• 14210-70-9 3-benzoyloxy-4,5-bis-benzoyloxymethyl-2-methyl-pyridine 
• 1136-52-3 (2,2,8-trimethyl-4H-[1,3]dioxino[4,5-c]pyridin-5-yl)methanol 
• 4372-46-7 3-hexadecanoyloxy-4,5-bis-hexadecanoyloxymethyl-2-methyl-pyridine 
• 948-00-5 1,5-dihydro-3,3,8-trimethyl<1,3>dioxepino<5,6-y>pyridin-9-ol 
• 14210-71-0 3-benzoyloxy-4-benzoyloxymethyl-5-hydroxymethyl-2-methyl-pyridine 
• 20905-66-2 2-Methyl-3-hydroxy-4-formyl-5-hydroxymethylpyridine oxime 
• 122776-11-8 5-(3-phenyl-2-propenyloxy)-6-methyl-3,4-bis(hydroxymethyl)pyridine hydrochloride 
• 77-76-9 2,2-dimethoxy-propane 
• 791724-87-3 5-chloromethyl-2,4-dimethyl-pyridin-3-ol 
• 943315-20-6 5-chloromethyl-3-methoxy-2,4-dimethylpyridine 

Relevant articles and documents

The cobalt way to vitamin B6. Regioselective construction of the tetrasubstituted pyridine nucleus by cobalt-catalyzed alkyne-nitrile cooligomerizations

Cocyclization of bis(trimethylsilyl)- and bis(trimethylstannyl)di-2-propynyl ether with acetonitrile provides a synthetic entry into 1,3-dihydro-6-methyl-4,7-bis(trimethylsilyl)- and bis(trimethylstannyl)-furo[3,4-c]pyridines. Regioselective electrophilic substitution of the respective silyl or stannyl groups allows for a regiocontrolled construction of tetrasubstituted pyridines. This method has been applied to a total synthesis of vitamin B6.

Method for environmentally friendly preparation of vitamin B6 and recycling of tail gas

The invention relates to a method for environmentally friendly preparation of vitamin B6 and recycling of tail gas. The method comprises the following steps: carrying out a catalytic formylating reaction on carbon monoxide, hydrogen and 2-cyano-2-cis-butene-1,4-diol which is used as a starting material to prepare a 2-hydroxymethyl-3-cyano-4-hydroxy-n-butyraldehyde intermediate, condensing the intermediate with 2-aminopropionate or 2-aminopropionate hydrochloride, and carrying out salt formation to prepare the vitamin B6. The method does not use a 4-methyl-5-alkoxyoxazole intermediate that is expensive and generates a large amount of wastewater in the production process, and allows the tail gas to be recycled in synthesis of the starting raw material, so the method has the advantages of environmentally friendly process, high reaction selectivity, high product purity, high atom economy, and suitableness for the green industrial production of the vitamin B6.

Method for preparing vitamin B6 by reducing 2-methyl-3-hydroxypyridine-4,5-diformic ether

The invention discloses a method for preparing vitamin B6 by reducing 2-methyl-3-hydroxypyridine-4,5-diformic ether. 2-methyl-3-hydroxypyridine-4,5-diformic ether is dissolved into a solvent, sodium borohydride or potassium borohydride, lewis acid and tertiary amine are then sequentially added, and heating reaction is then carried out for 2 to 4 hours; after the reaction is completed, system temperature is lowered to be less than or equal to 10 DEG C, 10 percent ammonium chloride is then added, pH is regulated to be neutral, filtration enrichment and extraction are carried out, HCl gas is injected, and after concentration, standing is performed for crystallization, filtration and drying to obtain a crude product of vitamin B6. In the technical solution, under the joint action of sodium borohydride or potassium borohydride, lewis acid and tertiary amine, 2-methyl-3-hydroxypyridine-4,5-diformic ether is reduced to prepare vitamin B6. In the whole operation process, the adopted solvent does not need to undergo anhydrous treatment, high-pressure equipment does not need to be adopted as well, and the operation process is carried out under mild conditions.

A process for preparing vitamin B by the malic acid6 The method of

The present invention relates to a method of using malic acid to prepare vitamin B6. The method comprises: using malic acid as a starting material; carrying out a hydroxymethylation reaction on the malic acid and formaldehyde in the presence of a basic catalyst to generate 2-hydroxy-2,3-dimethylol butanedioic acid; performing acid catalysis and lactonization for ring-forming to obtain 1H,4H-dihydrofuro[3,4-c]dihydrofuran-1,4-diketone (III); under base catalysis, condensing the obtained compound III and nitro ethane to obtain a compound IV; reducing the compound IV by using sodium borohydride or potassium borohydride to obtain a compound V; performing catalytic hydrogenation on the compound V to obtain a compound VI; and performing hydrolysis and ring-forming on the compound VI in an ethanol-hydrochloric acid system to obtain vitamin B6. According to the method of the present invention, the use of the 4-methyl-5-alkoxyl oxazole intermediate that is expensive and of which the preparation process causes pollution is avoid; the raw materials are inexpensive and readily available; the process is short; and the cost is low. The method in the present invention is simple in operation, less in wastewater discharge, highly environmentally friendly, and suitable for green industrial production of VB6.

Vitamin B6 for the continuous preparation of

The invention discloses a continuous preparation method of vitamin B6; in a continuous reaction device with multiple series-connection kettles, 4-methyl-5-ethoxy oxazole and 2-isopropyl-4,7-dihydro-1,3-dioxepin are subjected to a Diels-Alder addition reaction, a key intermediate compound represented by the formula IV is obtained, and the key intermediate compound represented by the formula IV is further subjected to aromatization and acidolysis to obtain the vitamin B6. According to the method, the damage degree of the reactants and the product is reduced, the occurrence of side reactions can be reduced, the reaction selectivity and the product yield and production efficiency are improved, and the high-purity vitamin B6 can be obtained.

Vitamin B6 synthesis method (by machine translation)

The present invention provides a vitamin B6 preparation method, in particular, the method of the invention in an inert solvent, the 4 - methyl - 5 - ethoxy - 2 - carboxyl oxazole and 2 - n-propyl - 4, 7 - dihydro - 1, 3 - British two wicked age to one-step reaction, thereby obtaining a preparation of vitamin B6 in the middle of the key type III compound. The method of the invention has small pollution, short reaction route and the like. (by machine translation)

Vitamin B6 Intermediate 4 - methyl - 5 - alkyl silicon oxygen radical wicked zuo, its preparation method and process for producing vitamin B6 The method of

The invention relates to a vitamin B6 intermediate 4-methyl-5-alkylsiloxane oxazole, a preparation method thereof as well as a method for preparing the vitamin B6. 4-methyl-5-alkylsiloxane oxazole has the structure shown as the formula I. 2-alanine and formaldehyde or paraformaldehyde are subjected to N-hydroxymethylation and lactonization in a solvent under the action of an acid catalyst to obtain 4-methyl-tetrahydro-oxazole-5-ketone (II), the ketone is not separated and is directly subjected to chloro substitution, silicon etherification and an elimination reaction in the presence of an acid-binding agent to generate 4-methyl-5-alkylsiloxane oxazole (I). 4-methyl-5-alkylsiloxane oxazole and 2-n-propyl-1,3-dioxo-5-cycloheptene are subjected to addition and hydrolysis to prepare the vitamin B6. The process is short, the operation is easy, little wastewater is produced, safety and environmental protection are realized, the reaction selectivity is good, a product is low in cost and high in purity, and industrial production is facilitated better.

Method for preparing vitamin B6 from 2-methyl-2-cyclopentenone

The invention relates to a method for preparing vitamin B6 from 2-methyl-2-cyclopentenone. The method comprises the steps that 2-methyl-2-cyclopentenone is taken as a starting raw material and reacts with formaldehyde through a hydroxymethylation reaction under catalysis of a basic catalyst to generate 4,5-dihydroxyl-2-methyl-2-cyclopentenone; separation is not conducted, 4,5-dihydroxyl-2-methyl-2-cyclopentenone is ozonized to obtain 2-3-dihydroxyl-4,5-dioxo-n-hexaldehyde, and obtained 2-3-dihydroxyl-4,5-dioxo-n-hexaldehyde and ammonia are directly subjected to condensation and hydrochloric acid acidizing to prepare the vitamin B6. The method is short in technological process, high in atom utilization rate of the adopted raw materials, low in product cost, little in wastewater discharge, good in environmental friendliness and suitable for industrialized production of the VB6.

Improved oxazole Method for the Practical and Efficient Preparation of Pyridoxine Hydrochloride (Vitamin B6)

Vitamin B6, a well-studied vitamin B, has been synthesized using an oxazole method for the past 20 years. The oxazole method provided 56.2% overall yield but also generated safety, environmental, and health problems, such as using toxic benzene as solvent and unstable, corrosive, and pollutive HCl and POCl3 as reagents. To use the same equipment but the least amount of toxic agents, we developed new reaction conditions for the early steps. For example, we successfully replaced toxic HCl/benzene conditions with NaHSO4/PhCH3 conditions and also developed a novel and efficient dehydrating agent trichloroisocyanuric acid/Ph3P/Et 3N to synthesize the key intermediate 5-butoxy-4-methyl oxazole, instead of using phosphorus oxychloride. These improvements resolved safety, waste avoidance, and workup issues that plagued the previous methodologies. Our process comprised six easy synthetic steps and generated vitamin B6 with 99.4% purity in 56.4% overall yield.

MANUFACTURE OF VITAMIN B6

The present invention relates to a process for the manufacture of pyridoxamine, pyridoxine and further clodely related 3-hydroxy-pyridine derivatives and of acid salts thereof. Pyridoxamine and pyridoxine belong to the vitamin B6 group. This new multistep process is represented schematically in the following Reaction Scheme (formula (I)).