63-42-3

Basic information

• Product Name: Lactose
• Synonyms: Aletobiose;Galactinum;lactose,anhydrous;Osmolactan;Saccharum lactin;saccharumlactin;LACTOBIOSE;LACTIN
• CAS NO: 63-42-3
• Molecular Formula: C12H22O11
• Molecular Weight: 342.3
• EINECS: 200-559-2
• Product Categories: Dextrins、Sugar & Carbohydrates;medicine excipents;Inhibitors;Imidazoles
• Mol File: 63-42-3.mol
• Article Data: 0

Chemical Properties

• Melting Point: 222.8°C
• Boiling Point: 397.76°C (rough estimate)
• Flash Point: 357.8 °C
• Appearance: White to Off-white/Powder
• Density: 1.5300
• Vapor Pressure: 1.08E-20mmHg at 25°C
• Refractive Index: 1.5376 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Freely but slowly soluble in water, practically insoluble in ethanol (96 per cent).
• PKA: 12.39±0.20(Predicted)
• Water Solubility: 5-10 g/100 mL at 20 ºC
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 93796
• CAS DataBase Reference: Lactose(CAS DataBase Reference)
• NIST Chemistry Reference: Lactose(63-42-3)
• EPA Substance Registry System: Lactose(63-42-3)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 2
• RTECS: OD9625000
• TSCA: Yes
• Hazardous Substances Data: 63-42-3(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 63-42-3 differently. You can refer to the following data:
1. white crystals or powder
2. Anhydrous lactose occurs as white to off-white crystalline particles or powder. Several different brands of anhydrous lactose are commercially available which contain anhydrous b-lactose and anhydrous a-lactose. Anhydrous lactose typically contains 70–80% anhydrous b-lactose and 20–30% anhydrous a-lactose.

Uses

Different sources of media describe the Uses of 63-42-3 differently. You can refer to the following data:
1. A disaccharide sugar present in milk.
2. Lactose is a disaccharide carbohydrate that occurs in mammalian milk except that of the whale and the hippopotamus. it is princi- pally obtained as a cows’ milk derivative. it is also termed milk sugar and it is a reducing sugar consisting of glucose and galactose. its most common commercial form is alpha-monohydrate, with the beta-anhydride form available to a lesser extent. all forms in solution will equilibrate to a beta:alpha ratio of 62.25:37.75 at 0°c. it is about one-sixth as sweet as sugar and is less soluble. it functions as a flow agent, humectant, crystallization control agent, and sweetener. it is used in baked goods for flavor, browning, and tenderizing and in dry mixes as an anticaking agent.
3. D-Lactose is used for the culture of lactic acid metabolizing bacteria, lactic acid bacteria. D-Lactose is used to identify and characterized galectins.

Definition

A sugar found in milk. It is a disaccharide composed of glucose and galactose units.

Production Methods

There are two anhydrous forms of lactose: a-lactose and b-lactose. The temperature of crystallization influences the ratio of a- and blactose. The anhydrous forms that are commercially available may exhibit hygroscopicity at high relative humidities. Anhydrous lactose is produced by roller drying a solution of lactose above 93.5°C. The resulting product is then milled and sieved. Two anhydrous a-lactoses can be prepared using special drying techniques: one is unstable and hygroscopic; the other exhibits good compaction properties. However, these materials are not commercially available.

General Description

Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

Air & Water Reactions

Water soluble.

Reactivity Profile

Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.

Health Hazard

ACUTE/CHRONIC HAZARDS: Lactose should be considered toxic.

Pharmaceutical Applications

Anhydrous lactose is widely used in direct compression tableting applications, and as a tablet and capsule filler and binder. Anhydrous lactose can be used with moisture-sensitive drugs due to its low moisture content. It may also be used in intravenous injections.

Safety

Lactose is widely used in pharmaceutical formulations as a diluent and filler-binder in oral capsule and tablet formulations. It may also be used in intravenous injections. Adverse reactions to lactose are largely due to lactose intolerance, which occurs in individuals with a deficiency of the intestinal enzyme lactase, and is associated with oral ingestion of amounts well over those found in solid dosage forms.

storage

Mold growth may occur under humid conditions (80% RH and above). Lactose may develop a brown coloration on storage, the reaction being accelerated by warm, damp conditions. At 80°C and 80% RH, tablets containing anhydrous lactose have been shown to expand 1.2 times after one day. Lactose anhydrous should be stored in a well-closed container in a cool, dry place.

Purification Methods

-Lactose crystallises from water below 93.5o as the hydrate which can be dried at 80o/14mm. [Horst Recl Trav Chim, Pays-Bas 72 878 1953, Beilst 17 III/IV 3066.]

Incompatibilities

Lactose anhydrous is incompatible with strong oxidizers. When mixtures containing a hydrophobic leukotriene antagonist and anhydrous lactose or lactose monohydrate were stored for six weeks at 40°C and 75% RH, the mixture containing anhydrous lactose showed greater moisture uptake and drug degradation. Studies have also shown that in blends of roxifiban acetate (DMP-754) and lactose anhydrous, the presence of lactose anhydrous accelerated the hydrolysis of the ester and amidine groups. Lactose anhydrous is a reducing sugar with the potential to interact with primary and secondary amines (Maillard reaction) when stored under conditions of high humidity for extended periods.

Regulatory Status

GRAS listed. Included in the FDA Inactive Ingredients Database (IM, IV: powder for injection solution; IV and sublingual preparations; oral: capsules and tablets; powder for inhalation; vaginal). Included in nonparenteral and parenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.

InChI:InChI=1/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3-,4-,5+,6+,7-,8-,9-,10-,11?,12+/m1/s1

Synthetic route

β-D-glucose (492-61-5) + (E)-3-Ureido-but-2-enoic acid ethyl ester (5435-44-9, 22243-66-9) → D-(+)-lactose (63-42-3)

Conditions	Yield
at 175℃; under 15 Torr;

acetic acid (64-19-7) + 2’-fucosyllactose (41263-94-9) → L-Fucose (2438-80-4) + D-(+)-lactose (63-42-3)

1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose (3616-19-1, 5328-50-7, 5346-90-7, 6291-42-5, 6920-00-9, 20764-63-0, 20880-60-8, 20880-65-3, 22352-19-8, 23973-20-8, 32447-69-1, 34213-32-6, 52554-32-2, 53956-64-2, 56907-29-0, 56994-12-8, 56994-13-9, 57128-38-8, 67650-36-6, 68036-17-9, 68036-19-1, 78215-50-6, 78215-51-7, 79549-48-7, 80446-82-8, 85249-04-3, 93221-83-1, 93779-27-2, 111407-83-1, 111407-84-2, 111407-85-3, 120328-65-6, 123809-59-6, 132341-46-9, 132341-47-0, 132341-49-2, 145307-94-4) → D-(+)-lactose (63-42-3)

Conditions	Yield
With methanol; barium methoxide

β-D-glucose (492-61-5) + β-D-galactose → D-(+)-lactose (63-42-3)

Conditions	Yield
With zinc(II) chloride at 175℃; under 15 Torr;

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) + O2,O3;O5,O6-diisopropylidene-D-glucose-diethylacetal → D-(+)-lactose (63-42-3)

Conditions	Yield
With chloroform; iodine; silver(l) oxide anschl. mit methanol. NaOH und dann mit wss. Essigsaeure;

hydrogenchloride (7647-01-0) + 2’-fucosyllactose (41263-94-9) → L-Fucose (2438-80-4) + D-(+)-lactose (63-42-3)

meso-erythritol (909878-64-4) + L-Tartaric acid (87-69-4) → (+)-proto-quercitol (488-73-3) + Sucrose (57-50-1) + D-(+)-lactose (63-42-3) + pinitol

D-(+)-lactose (63-42-3) → lactobionic acid (96-82-2, 534-41-8, 534-42-9, 51267-45-9, 58459-39-5, 69728-97-8)

Conditions	Yield
With oxygen for 2h; Reagent/catalyst;	100%
With sodium hydroxide; palladium dichloride; potassium hexacyanoferrate(III) In water at 35℃; Rate constant; Thermodynamic data; Eact, ΔS(excit.), ΔH(excit.), ΔG(excit.);
With sodium hydroxide; potassium hexacyanoferrate(III) In water at 35℃; Rate constant; Thermodynamic data; Eact, ΔS(excit.), ΔH(excit.), ΔG(excit.);

tetradecylamine (2016-42-4) + D-(+)-lactose (63-42-3) → N-tetradecyl lactosamine

Conditions	Yield
at -10℃;	92%

n-Dodecylamine (124-22-1) + D-(+)-lactose (63-42-3) → N-dodecyl lactosamine

Conditions	Yield
at -10℃;	90%

3,6-dioxa-1,8-diaminooctane (929-59-9) + D-(+)-lactose (63-42-3) → 1,8-bis(1-deoxy-D-lactitol-1-ylamino)-3,6-dioxaoctane

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol; water at 40℃; under 6750.68 Torr; for 24h;	87%

ammonium carbamate (1111-78-0) + D-(+)-lactose (63-42-3) → (2S,3R,4S,5R,6R)-2-((2R,3S,4R,5R,6R)-6-Amino-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol; compound with carbamic acid

Conditions	Yield
With ammonium hydroxide In methanol at 37℃; for 20h;	85%

carbonic acid bis(1-isopropylhydrazide) dihydrochloride + D-(+)-lactose (63-42-3) → 1'S,2'R,3'R,4'R-2,4-diisopropyl-6-(3'-α-D-galactopyranosyl-1',2',4',5'-tetrahydroxypentyl)-1,2,4,5-tetrazinan-3-one

Conditions	Yield
With sodium acetate In water at 20℃;	83%

2-mercaptoacetohydrazide (760-30-5) + D-(+)-lactose (63-42-3) → D-lactose (2-sulfanylacetyl)hydrazone

Conditions	Yield
In water at 25℃; for 72h;	70%

acetyl chloride (75-36-5) + D-(+)-lactose (63-42-3) → 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranosyl chloride (14227-58-8)

Conditions	Yield
With indium(III) triflate at 20℃; for 5h;	65%

2-mercaptobenzoic acid hydrazide (24611-43-6) + D-(+)-lactose (63-42-3) → D-lactose (2-sulfanylbenzoyl)hydrazone

Conditions	Yield
In water at 25℃; for 72h;	65%

D-(+)-lactose (63-42-3) → C12H14O28S6(6-)*6Na(1+)

Conditions	Yield
Stage #1: D-(+)-lactose With triethylamine sulfur trioxide In N,N-dimethyl-formamide at 120℃; for 0.166667h; Inert atmosphere; Stage #2: In water	64%

calcium 3-{[(2S,4R)-1-{[1,1'-biphenyl]-4-yl}-5-ethoxy-4-methyl-5-oxopentan-2-yl]carbamoyl}propanoate + D-(+)-lactose (63-42-3) → C24H28NO5(1-)*Na(1+)*C12H22O11

Conditions	Yield
Stage #1: calcium 3-{[(2S,4R)-1-{[1,1'-biphenyl]-4-yl}-5-ethoxy-4-methyl-5-oxopentan-2-yl]carbamoyl}propanoate With hydrogenchloride In water; acetonitrile at 25℃; Stage #2: With sodium 2-ethylhexanoic acid In acetonitrile at 40℃; for 12h; Stage #3: D-(+)-lactose In acetonitrile at 0℃; for 2h;	59.6%

vinyl laurate (2146-71-6) + D-(+)-lactose (63-42-3) → lauric acid (143-07-7) + lactose (C-6')-monolaurate

Conditions	Yield
Lipozyme, immobilized from Mucor miehei (MM) In tert-Amyl alcohol at 55℃; for 72h; Product distribution / selectivity; Molecular sieve; Enzymatic reaction;	A n/a B 52.4%

4-nitrophenyl α-D-galactoside (7493-95-0) + D-(+)-lactose (63-42-3) → α-D-galactopyranosyl(1->6)-β-D-galactopyranosyl-(1->4)-D-glucopyranose

Conditions	Yield
With recombinant Aspergillus nidulans FGSC GH36 α-galactosidase at 37℃; for 3h; pH=5; aq. acetate buffer; Enzymatic reaction; regioselective reaction;	38%

oseltamivir phosphate (204255-11-8) + D-(+)-lactose (63-42-3) → (3R,4R,5S)-ethyl 4-acetamido-N-(1'-deoxylactitol-1'-yl)-5-amino-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate (1296084-57-5)

Conditions	Yield
Stage #1: oseltamivir phosphate; D-(+)-lactose at 20℃; for 1h; pH=7.4; aq. phosphate buffer; Stage #2: With sodium cyanoborohydride at 80℃; for 6h; aq. phosphate buffer;	36%

1,6-Hexanediamine (124-09-4) + D-(+)-lactose (63-42-3) → 1,6-bis(1-deoxy-D-lactitol-1-ylamino)hexane

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol; water at 40℃; under 6750.68 Torr; for 24h;	35%

propargyl alcohol (107-19-7) + D-(+)-lactose (63-42-3) → 1-propynyl-β-D-galactopyranoside (151168-59-1)

Conditions	Yield
With Aspergillus oryzae β-galactosidase at 25℃; pH=4.5; aq. acetate buffer; Enzymatic reaction;	26%

1,4-dihydroxybut-2-yne (110-65-6) + D-(+)-lactose (63-42-3) → 4-hydroxybut-2-yn-1-yl β-D-galactopyranoside (1190202-83-5)

Conditions	Yield
With Aspergillus oryzae β-galactosidase at 25℃; pH=4.5; aq. acetate buffer; Enzymatic reaction;	21%

benzoyl chloride (98-88-4) + D-(+)-lactose (63-42-3) → 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1→4)-1,2,6-tri-O-benzoyl-β-D-glucopyranose (41093-35-0)

Conditions	Yield
With sodium hydroxide at 20℃; for 1h;	20%

1-butyn-4-ol (927-74-2) + D-(+)-lactose (63-42-3) → 1-O-but-3-ynyl-α-D-galactopyranoside (1190202-80-2)

Conditions	Yield
With Aspergillus oryzae β-galactosidase at 25℃; pH=4.5; aq. acetate buffer; Enzymatic reaction;	18%

pent-1-yn-5-ol (5390-04-5) + D-(+)-lactose (63-42-3) → pent-4-yn-1-yl β-D-galactopyranoside (1190202-81-3)

Conditions	Yield
With Aspergillus oryzae β-galactosidase at 25℃; pH=4.5; aq. acetate buffer; Enzymatic reaction;	17%

hex-2-yn-1-ol (764-60-3) + D-(+)-lactose (63-42-3) → hex-2-yn-1-yl β-D-galactopyranoside (1190202-86-8)

Conditions	Yield
With Aspergillus oryzae β-galactosidase at 25℃; pH=4.5; aq. acetate buffer; Enzymatic reaction;	16%

Upstream product

• 492-61-5 β-D-glucose 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 64-19-7 acetic acid 
• 41263-94-9 2′-fucosyllactose 
• 3616-19-1 1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 7647-01-0 hydrogenchloride 
• 909878-64-4 meso-erythritol 
• 87-69-4 L-Tartaric acid 

Downstream Products

• 13101-54-7 lactosucrose 
• 25197-87-9 lactose-isonicotinoylhydrazone 
• 120971-58-6 O¹,O²,O³,O⁶-Tetrakis-(2-methoxy-phenoxycarbonyl)-O⁴-[tetrakis-O-(2-methoxy-phenoxycarbonyl)-β-D-galactopyranosyl]-ξ-D-glucopyranose 
• 4753-07-5 2,3,6,2',3',4',6'-hepta-O-acetyl-lactosyl bromide 
• 117898-43-8 1-[3-(2,5-dichloro-phenyl)-1-p-tolyl-triaz-2-eno]-O⁴-β-D-galactopyranosyl-1-deoxy-D-fructose 
• 67911-91-5 O⁴-β-D-galactopyranosyl-D-glucose-benzoylhydrazone 
• 78-98-8 2-oxopropanal 
• 13992-23-9 (2R,3S,4S,5R)-6,6-bis(phenylthio)hexane-1,2,3,4,5-pentaol 
• 126740-20-3 O⁴-β-D-galactopyranosyl-D-glucose-phenylimine 
• 7707-85-9 pyruvaldehyde bis-phenylhydrazone 
• 119041-75-7 O⁴-β-D-galactopyranosyl-D-arabino-[2]hexosulose-1-(methyl-phenyl-hydrazone)-2-(4-nitro-phenylhydrazone) 
• 67912-08-7 O⁴-β-D-galactopyranosyl-D-glucose-(toluene-4-sulfonylhydrazone)