11041-94-4

Basic information

• Product Name: Demethyl
• Synonyms: Demethyl;1,2,3,4-Tetrahydro-1-((4-hydroxyphenyl)methyl)-6,7-isoquinolinediol hydrochloride;Higenamine hydrochloride;6,7-dihydroxy-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline;6,7-Dihydroxy-1-(4-Hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride;6,7-Isoquinolinediol,1,2,3,4-tetrahydro-1-[(4-hydroxyphenyl)methyl]-, hydrochloride (1:1);1-(4-Hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol hydrochloride;norcoclaurine hcl
• CAS NO: 11041-94-4
• Molecular Formula: C₁₆H₁₇NO₃*ClH
• Molecular Weight: 307.77202
• EINECS: 1592732-453-0
• Mol File: 11041-94-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 522.4 °C at 760 mmHg
• Flash Point: 209.6 °C
• Appearance: white powder
• Vapor Pressure: 1.56E-11mmHg at 25°C
• CAS DataBase Reference: Demethyl(CAS DataBase Reference)
• NIST Chemistry Reference: Demethyl(11041-94-4)
• EPA Substance Registry System: Demethyl(11041-94-4)

Safety Data

• Hazardous Substances Data: 11041-94-4(Hazardous Substances Data)

Usage

Description

Demethyl, also known as Glycerol, is a simple polyol compound that is widely used in various industries due to its unique properties. It is a colorless, odorless, and viscous liquid with a sweet taste. Glycerol is hygroscopic, meaning it can absorb moisture from the air, and it is also a humectant, which helps to retain moisture in various applications. Its chemical structure allows it to form hydrogen bonds with other molecules, making it a versatile compound with numerous uses.

Uses

Used in the Food and Beverage Industry:
Demethyl is used as a humectant and sweetener in the food and beverage industry. Its ability to retain moisture helps to maintain the texture and freshness of various products, such as baked goods, confectionery, and beverages. Additionally, its sweet taste enhances the flavor of these products.
Used in the Pharmaceutical Industry:
In the pharmaceutical industry, Demethyl is used as a solvent for various drugs and as a base for liquid oral and topical medications. Its ability to dissolve a wide range of substances makes it an ideal choice for drug formulation. Furthermore, its humectant properties help to maintain the stability and shelf life of medications.
Used in the Cosmetics and Personal Care Industry:
Demethyl is used as a moisturizer and humectant in cosmetics and personal care products, such as lotions, creams, and shampoos. Its ability to retain moisture helps to keep the skin and hair hydrated, promoting a healthy appearance and feel.
Used in the Textile Industry:
In the textile industry, Demethyl is used as a humectant and plasticizer in the production of synthetic fibers, such as polyester and spandex. Its ability to retain moisture helps to maintain the flexibility and softness of these fibers, improving their overall quality and performance.
Used in the Automotive Industry:
Demethyl is used as a component in the production of antifreeze and coolants for automotive applications. Its ability to lower the freezing point of water and raise the boiling point makes it an essential ingredient in these products, helping to protect engines from extreme temperatures.
Used in the Energy Industry:
In the energy industry, Demethyl is used as a component in the production of biodiesel fuel. Its compatibility with various feedstocks and its ability to improve the fuel's properties, such as viscosity and lubricity, make it a valuable additive in this application.
Used in the Agricultural Industry:
Demethyl is used as a humectant and moisturizer in the agricultural industry, particularly in the production of fertilizers and soil conditioners. Its ability to retain moisture helps to improve the water-holding capacity of the soil, promoting healthy plant growth and increased crop yields.

Toxicity

The safety of orally administered higenamine hydrochloride in humans is unknown. During a study of acute toxicity, mice were orally administered the compound at a dose of 2 g per kg of bodyweight. No mice died during the study.In human trials of intravenous higenamine, subjects who received higenamine reported shortness of breath, racing heart, dizziness, headaches, chest tightness.

InChI:InChI=1/C16H17NO3.ClH/c18-12-3-1-10(2-4-12)7-14-13-9-16(20)15(19)8-11(13)5-6-17-14;/h1-4,8-9,14,17-20H,5-7H2;1H

Synthetic route

6,7-bisbenzyloxy-1-(4-benzyloxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (117765-29-4) → 6,7-dihydroxy-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (11041-94-4)

Conditions	Yield
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol for 2h;

2-[4-(benzyloxy)phenyl]acetonitrile (838-96-0) → 6,7-dihydroxy-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (11041-94-4)

Conditions

Yield

Multi-step reaction with 6 steps 1: potassium hydroxide, water / ethane-1,2-diol / 18 h / Heating 2: oxalyl chloride, DMF / benzene / 1 h / 20 °C 3: sodium hydrogen carbonate / CH2Cl2; H2O / 1.5 h 4: phosphorus oxychloride / acetonitrile / 0.42 h / Heating 5: sodium borohydride / methanol / 0.75 h / 0 °C 6: hydrogen, conc. hydrochloric acid / 10percent palladium-charcoal / ethanol / 2 h View Scheme

3,4-bis(benzyloxy)-β-nitrostyrene (1699-54-3) → 6,7-dihydroxy-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (11041-94-4)

Conditions	Yield
Multi-step reaction with 5 steps 1: 70 percent / lithium aluminium hydride / tetrahydrofuran / 1.25 h / Heating 2: sodium hydrogen carbonate / CH2Cl2; H2O / 1.5 h 3: phosphorus oxychloride / acetonitrile / 0.42 h / Heating 4: sodium borohydride / methanol / 0.75 h / 0 °C 5: hydrogen, conc. hydrochloric acid / 10percent palladium-charcoal / ethanol / 2 h View Scheme

2-(4-(benzyloxy)phenyl)acetyl chloride (39188-62-0) → 6,7-dihydroxy-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (11041-94-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydrogen carbonate / CH2Cl2; H2O / 1.5 h 2: phosphorus oxychloride / acetonitrile / 0.42 h / Heating 3: sodium borohydride / methanol / 0.75 h / 0 °C 4: hydrogen, conc. hydrochloric acid / 10percent palladium-charcoal / ethanol / 2 h View Scheme

2-[4-(benzyloxy)benzyl]acetic acid (6547-53-1) → 6,7-dihydroxy-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (11041-94-4)

Conditions	Yield
Multi-step reaction with 5 steps 1: oxalyl chloride, DMF / benzene / 1 h / 20 °C 2: sodium hydrogen carbonate / CH2Cl2; H2O / 1.5 h 3: phosphorus oxychloride / acetonitrile / 0.42 h / Heating 4: sodium borohydride / methanol / 0.75 h / 0 °C 5: hydrogen, conc. hydrochloric acid / 10percent palladium-charcoal / ethanol / 2 h View Scheme

2-(3,4-bis (phenylmethoxy)phenyl)ethylamine hydrochloride (1699-56-5) → 6,7-dihydroxy-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (11041-94-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium hydrogen carbonate / CH2Cl2; H2O / 1.5 h 2: phosphorus oxychloride / acetonitrile / 0.42 h / Heating 3: sodium borohydride / methanol / 0.75 h / 0 °C 4: hydrogen, conc. hydrochloric acid / 10percent palladium-charcoal / ethanol / 2 h View Scheme

N-(3,4-dibenzyloxyphenethyl)-4-benzyloxyphenylacetamide (23428-48-0) → 6,7-dihydroxy-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (11041-94-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: phosphorus oxychloride / acetonitrile / 0.42 h / Heating 2: sodium borohydride / methanol / 0.75 h / 0 °C 3: hydrogen, conc. hydrochloric acid / 10percent palladium-charcoal / ethanol / 2 h View Scheme

6,7-bisbenzyloxy-1-(4-benzyloxybenzyl)-3,4-dihydroisoquinoline hydrochloride (23428-49-1) → 6,7-dihydroxy-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (11041-94-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium borohydride / methanol / 0.75 h / 0 °C 2: hydrogen, conc. hydrochloric acid / 10percent palladium-charcoal / ethanol / 2 h View Scheme

Upstream product

• 23428-49-1 6,7-bisbenzyloxy-1-(4-benzyloxybenzyl)-3,4-dihydroisoquinoline hydrochloride 
• 23428-48-0 N-(3,4-dibenzyloxyphenethyl)-4-benzyloxyphenylacetamide 
• 1699-56-5 2-(3,4-bis (phenylmethoxy)phenyl)ethylamine hydrochloride 
• 6547-53-1 2-[4-(benzyloxy)benzyl]acetic acid 
• 39188-62-0 2-(4-(benzyloxy)phenyl)acetyl chloride 
• 1699-54-3 3,4-bis(benzyloxy)-β-nitrostyrene 
• 838-96-0 2-[4-(benzyloxy)phenyl]acetonitrile 
• 117765-29-4 6,7-bisbenzyloxy-1-(4-benzyloxybenzyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride 

Relevant articles and documents

Biosynthesis. Part 24. Speculative Incorporation Experiments with 1-Benzylisoquinolines and a Logical Approach via C6-C2 and C6-C3 Precursors to the Biosynthesis of Hasubanonine and Protostephanine

Many possible 1-benzyltetrahydroisoquinolines have been examined as possible advanced precursors of the alkaloids hasubanonine (1) and protostephanine (2) in Stephania japonica plants, but none was incorporated significantly.Administration of various precursor molecules having only one aromatic ring, such as tyrosine, has demonstrated that both alkaloids are derived from two different C6-C2 biogenetic units.The subsequent failure of further 1-benzyltetrahydroisoquinolines and bisphenethylamines to be incorporated suggested the intermediacy of either (a) modified 1-benzylisoquinolines or (b) trioxygenated C6-C2 building blocks.Precursors designed to examine the first possibility, such as 1-benzyl-3,4-dihydroisoquinolines or 1-benzyl-1-carboxytetrahydroisoquinolines, were not incorporated into (1) and (2) whereas two 3',4',5'-trioxygenated 2-phenylethylamines were incorporated.These findings allow further delineation of the requirements for later precursors of the alkaloids (1) and (2).