501-94-0

Basic information

• Product Name: 4-Hydroxyphenethyl alcohol
• Synonyms: 4-Hydroxyphenyl-2-ethanol;Tyrosol (antioxidant): 4-(2-hydroxyethyl)phenol;2-(4-Hydroxyphenyl)ethanol(p-HPEA);4-hydroxy-benzeneethano;4-hydroxy-Benzeneethanol;4-Hydroxyphenylethanol;beta-(4-Hydroxyphenyl)ethanol;beta-(p-Hydroxyphenyl)ethanol
• CAS NO: 501-94-0
• Molecular Formula: C₈H₁₀O₂
• Molecular Weight: 138.16
• EINECS: 207-930-8
• Product Categories: Inhibitors;Phenols;Alcohols and Derivatives;Benzhydrols, Benzyl & Special Alcohols;Benzene derivates;Alkohols;API intermediates;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Alcohols;Building Blocks;C7 to C8;Chemical Synthesis;Nutrition Research;Olea europaea (Olive);Organic Building Blocks;Oxygen Compounds;Phytochemicals by Plant (Food/Spice/Herb);chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 501-94-0.mol
• Article Data: 66

Chemical Properties

• Melting Point: 89-92 °C(lit.)
• Boiling Point: 195°C (18 mmHg)
• Flash Point: 139°C/1mm
• Appearance: Off-white to light beige/Crystals or Crystalline Powder
• Density: 1.0742 (rough estimate)
• Vapor Pressure: 0.00113mmHg at 25°C
• Refractive Index: 1.5590 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 124g/l
• PKA: 10.17±0.13(Predicted)
• Water Solubility: slightly soluble
• BRN: 1859884
• CAS DataBase Reference: 4-Hydroxyphenethyl alcohol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxyphenethyl alcohol(501-94-0)
• EPA Substance Registry System: 4-Hydroxyphenethyl alcohol(501-94-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-24/25-36
• WGK Germany: 3
• F: 10
• TSCA: Yes
• Hazardous Substances Data: 501-94-0(Hazardous Substances Data)

Usage

Description

Phenylalanine is an amino acid, which are the building blocks of proteins in your body. This molecule exists in two forms or arrangements: L-phenylalanine and D-phenylalanine. They’re nearly identical but have a slightly different molecular structure. The L-form is found in foods and used to produce proteins in your body, while the D-form can be synthesized for use in certain medical applications . Your body is unable to produce enough L-phenylalanine on its own, so it’s considered an essential amino acid that must be obtained through your diet. It’s found in a wide variety of foods — both plant and animal sources. In addition to its role in protein production, phenylalanine is used to make other important molecules in your body, several of which send signals between different parts of your body. Phenylalanine has been studied as a treatment for several medical conditions, including skin disorders, depression and pain. However, it can be dangerous for people with the genetic disorder phenylketonuria (PKU).

Health Benefits

Phenylalanine can be used to produce the molecule dopamine. Dopamine malfunction in the brain is associated with some forms of depression . One small 12-person study showed a possible benefit of a mixture of the D- and L-forms of this amino acid for treating depression, with 2/3 of patients showing improvement . However, there is minimal other support for phenylalanine’s effects on depression, and most studies have not found clear benefits. In addition to vitiligo and depression, phenylalanine has been studied for potential effects on: Pain: The D-form of phenylalanine may contribute to pain relief in some instances, though study results are mixed . Alcohol withdrawal: A small amount of research indicates that this amino acid, along with other amino acids, may help alleviate symptoms of alcohol withdrawal. Parkinson’s disease: Very limited evidence suggests that phenylalanine may be beneficial in treating Parkinson’s disease, but more studies are needed . ADHD: Currently, research does not indicate benefits of this amino acid for the treatment of attention deficit hyperactivity disorder (ADHD) .

Side effects

Phenylalanine is found in many protein-containing foods and is “generally recognized as safe” by the Food and Drug Administration (FDA) (27). The amount of this amino acid found in foods should not pose a risk for otherwise healthy individuals. What’s more, few or no side effects are generally observed at supplement doses of 23–45 mg per pound (50–100 mg per kg) of body weight (9Trusted Source, 13Trusted Source). However, it may be best for pregnant women to avoid taking phenylalanine supplements.

Uses

Different sources of media describe the Uses of 501-94-0 differently. You can refer to the following data:
1. L-phenylalanine (LPA) serves as a building block for the various proteins that are produced in the body. LPA can be converted to L-tyrosine (another amino acid ) and subsequently to L-dopa, norepinephrine, and epinephrine . LPA can also be converted (through a separate pathway) to phenylethylamine, a substance that occurs naturally in the brain and appears to elevate mood.
2. Phenolic antioxidant.
3. Tyrosol (Metoprolol EP Impurity G) is a phenolic antioxidant.

Chemical Properties

off-white to light beige crystals or crystalline

Definition

ChEBI: A phenol substituted at position 4 by a 2-hydroxyethyl group.

General Description

2-(4-Hydroxyphenyl)ethanol is a phenolic alcohol commonly present in olive mill wastewater.

Biochem/physiol Actions

Antioxidant found in olive oil.

InChI:InChI=1/C8H10O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,9-10H,5-6H2

Synthetic route

4-hydroxyphenylacetate (156-38-7) → p-hydroxyphenethyl alcohol (501-94-0)

Conditions	Yield
With sodium tetrahydroborate; Trimethyl borate; dimethyl sulfate In tetrahydrofuran at 20℃; for 1.5h;	98%
With sodium tetrahydroborate; iodine In tetrahydrofuran for 2h; Heating;	88%
With lithium aluminium tetrahydride In tetrahydrofuran at 67℃; for 2.5h;	88%

p-Coumaric Acid (7400-08-0) → 4-hydroxyphenylacetate (156-38-7) + p-hydroxyphenethyl alcohol (501-94-0)

Conditions	Yield
With β-D-glucose; oxygen for 18h; Reagent/catalyst; Enzymatic reaction;	A n/a B 97.3%

1-methylsulfanylmethoxy-4-(2-methylsulfanylmethoxy-ethyl)-benzene → p-hydroxyphenethyl alcohol (501-94-0)

Conditions	Yield
With methanol; iodine at 50℃; for 3.5h;	96%

1-(2-methoxy-ethoxymethoxy)-4-[2-(2-methoxy-ethoxymethoxy)-ethyl]-benzene → p-hydroxyphenethyl alcohol (501-94-0)

Conditions	Yield
With methanol; iodine at 50℃; for 48h;	96%

tert-butyl(4-(2-(tert-butyldimethylsilyloxy)ethyl)phenoxy)dimethylsilane (96013-68-2) → p-hydroxyphenethyl alcohol (501-94-0)

Conditions	Yield
With methanol; trimethylsilyl bromide at 20℃; for 5h; chemoselective reaction;	95%
With antimonypentachloride; water In acetonitrile at 20℃; for 0.166667h;	92%
With iron(III) p-toluenesulfonate hexahydrate In methanol for 26.25h; Reflux;	84%

1-(2-trimethylsilanyl-ethoxymethoxy)-4-[2-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-benzene → p-hydroxyphenethyl alcohol (501-94-0)

Conditions	Yield
With methanol; iodine at 50℃; for 10h;	95%

1-methoxymethoxy-4-(2-methoxymethoxy-ethyl)-benzene → p-hydroxyphenethyl alcohol (501-94-0)

Conditions	Yield
With methanol; iodine at 50℃; for 34h;	94%

Methyl 4-hydroxyphenylacetate (14199-15-6) → p-hydroxyphenethyl alcohol (501-94-0)

Conditions	Yield
With methanol; Na/SiO2 In tetrahydrofuran at 0 - 25℃; Bouveault-Blanc reduction; Inert atmosphere;	93%
With 5 wt% Re/TiO2; hydrogen In octane at 200℃; under 37503.8 Torr; for 24h; Autoclave; chemoselective reaction;	91%
With sodium tetrahydroborate In water for 8h; Ambient temperature;	90%

4-(2-bromoethyl)phenol (14140-15-9) → p-hydroxyphenethyl alcohol (501-94-0)

Conditions	Yield
Stage #1: 4-(2-bromoethyl)phenol With sodium acetate In water for 3h; Reflux; Stage #2: With sodium hydroxide In water for 0.5h; Inert atmosphere; Reflux;	88%

2-[4-(4-nitro-benzyloxy)-phenyl]-ethanol → p-hydroxyphenethyl alcohol (501-94-0) + p-toluidine (106-49-0)

Conditions	Yield
With magnesium In methanol at 20℃; for 10h;	A 83% B n/a

4-[2-(2-chloroacetyl)oxoethyl]phenyl-2-chloroacetate (1223454-88-3) → p-hydroxyphenethyl alcohol (501-94-0)

Conditions	Yield
With sodium tetrahydroborate In ethanol at 0 - 20℃; Inert atmosphere;	81%

C14H18O6 → p-hydroxyphenethyl alcohol (501-94-0)

Conditions	Yield
With sodium tetrahydroborate In ethanol at 20℃; for 1h;	81%

1-methoxymethoxy-4-(2-methoxymethoxy-ethyl)-benzene → p-hydroxyphenethyl alcohol (501-94-0) + 4-(2-methoxymethoxy-ethyl)-phenol

Conditions	Yield
sodium hydrogen sulfate; silica gel In dichloromethane at 20℃; for 1.5h;	A 12% B 76%

Methyl 4-hydroxyphenylacetate (14199-15-6) → p-hydroxyphenethyl alcohol (501-94-0) + 4-hydroxyphenylacetaldehyde (7339-87-9)

Conditions	Yield
With diisobutylaluminium hydride In toluene at -78℃; for 5h;	A 10% B 75%

2-(3,5-di-t-butyl-4-hydroxyphenyl)ethanol (3673-68-5) → p-hydroxyphenethyl alcohol (501-94-0)

Conditions	Yield
at 285 - 295℃; for 19h; Inert atmosphere;	72%

1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-(tert-butyl-diphenyl-silanyloxy)-benzene → p-hydroxyphenethyl alcohol (501-94-0) + 2-[4'-(tert-butyldiphenylsilyloxy)phenyl]ethanol (96013-93-3)

Conditions	Yield
With bismuth oxide perchlorate In dichloromethane at 45℃; for 3h;	A n/a B 65%

2-(3,5-di-t-butyl-4-hydroxyphenyl)ethanol (3673-68-5) → p-cresol (106-44-5) + benzofuran-5-ol (13196-10-6) + 4-Ethylphenol (123-07-9) + p-hydroxyphenethyl alcohol (501-94-0) + 1-[4-(2-hydroxyethyl)phenoxy]-2-(4'-hydroxyphenyl)ethane (1240059-73-7) + di[2-(4-hydroxyphenyl)]ethyl ether (501123-58-6) + C24H34O3 + 6-tert-butyl-5-hydroxybenzofuran (117516-54-8) + phenol (108-95-2)

Conditions	Yield
at 295 - 298℃; for 22h; Inert atmosphere;	A n/a B n/a C n/a D 55% E n/a F 40 g G n/a H n/a I n/a

...Expand

methanol (67-56-1) + 4-(trimethylsilylmethyl)phenyl methanesulfonate → p-cresol (106-44-5) + p-hydroxyphenethyl alcohol (501-94-0) + 1-methyl-1-phenylethyl alcohol (617-94-7) + 2-phenylethanol (60-12-8) + 4-tolyl mesylate (17177-63-8)

Conditions	Yield
With acetone Irradiation; Inert atmosphere;	A n/a B 8% C 8% D 8% E 23%

tyrosamine (51-67-2) → p-hydroxyphenethyl alcohol (501-94-0)

Conditions	Yield
With yeast

4-hydroxy-phenethyl iodide (6631-69-2) → p-hydroxyphenethyl alcohol (501-94-0)

Conditions	Yield
With water; silver(l) oxide

4-(2-chloroethyl)phenol (28145-35-9) → p-hydroxyphenethyl alcohol (501-94-0)

Conditions	Yield
With sodium acetate; acetic acid Erwaermen des Reaktionsprodukts mit Natronlauge;

N,N-dimethyltyramine (539-15-1) → p-hydroxyphenethyl alcohol (501-94-0)

Conditions	Yield
With yeast

4-Hydroxyphenylpyruvic acid (156-39-8) → p-hydroxyphenethyl alcohol (501-94-0)

Conditions	Yield
With yeast
Multi-step reaction with 2 steps 1: aq. phosphate buffer / 37 °C / Green chemistry; Enzymatic reaction 2: aq. phosphate buffer / 37 °C / Green chemistry; Enzymatic reaction View Scheme

L-tyrosine (60-18-4) → p-hydroxyphenethyl alcohol (501-94-0)

Conditions	Yield
With vinegar bacteria
Stage #1: L-tyrosine With recombinant parsley (Petroselinum crispum) aromatic acetaldehyde synthese Q06086 at 25℃; for 1h; pH=6.8; aq. phosphate buffer; Enzymatic reaction; Stage #2: With sodium tetrahydroborate In ethanol at 25℃; for 0.0833333h;
Multi-step reaction with 3 steps 1: aq. phosphate buffer / 37 °C / Green chemistry; Enzymatic reaction 2: aq. phosphate buffer / 37 °C / Green chemistry; Enzymatic reaction 3: aq. phosphate buffer / 37 °C / Green chemistry; Enzymatic reaction View Scheme

›Tyr (556-02-5, 556-03-6, 34537-57-0, 55520-40-6, 96946-98-4, 60-18-4) → p-hydroxyphenethyl alcohol (501-94-0)

Conditions	Yield
durch gaerende Hefe;
bei der Hefegaerung;
With lactic acid bacteria
Einw. von lebender Hefe bei der alkohol. Vergaerung des Zuckers;
Multi-step reaction with 2 steps 1: 270 °C / 12 - 25 Torr 2: yeast View Scheme

methanol (67-56-1) + osmanthuside B (97549-57-0, 94492-23-6) → p-hydroxyphenethyl alcohol (501-94-0) + methyl 4-hydroxycinnamate (3943-97-3)

Conditions	Yield
With acetyl chloride for 0.5h; Heating;

methanol (67-56-1) + fraxiformoside (142998-21-8) → p-hydroxyphenethyl alcohol (501-94-0) + isoligustroside (108789-18-0)

Conditions	Yield
for 40h; Heating;	A 13.8 mg B 53.2 mg

ligstroside (35897-92-8) → D-Glucose (2280-44-6) + p-hydroxyphenethyl alcohol (501-94-0)

Conditions	Yield
With potassium hydroxide In methanol at 60℃; for 2h;	A n/a B 2 mg

4-[2-(acetyloxy)ethyl]-4-hydroxy-2,5-cyclohexadien-1-one (94414-03-6) → p-hydroxyphenethyl alcohol (501-94-0) + rengyol (93675-85-5, 101489-38-7) + trans-1-(2-hydroxyethyl)cyclohexane-1,4-diol (101489-38-7)

Conditions	Yield
With sodium tetrahydroborate In methanol Ambient temperature;	A 25 mg B 15 mg C 11 mg

p-hydroxyphenethyl alcohol (501-94-0) → 4-(2-bromoethyl)phenol (14140-15-9)

Conditions	Yield
With PS-triphenylphosphine; bromine In dichloromethane at 0℃; for 1h;	100%
With diphenylphosphino-polystyrene; carbon tetrabromide In dichloromethane at 40℃; for 3.5h;	100%
With hydrogen bromide In water at 80℃; for 16h;	100%

vinyl acetate (108-05-4) + p-hydroxyphenethyl alcohol (501-94-0) → 2-(4-hydroxyphenyl)ethyl acetate (58556-55-1)

Conditions	Yield
With Candida cylindracea lipase In hexane for 4h;	100%
With Candida antartica lipase B In tetrahydrofuran at 20℃; for 4h; Enzymatic reaction; chemoselective reaction;	100%
With 1,3-dichlorotetrabutyldistannoxane In tetrahydrofuran at 30℃; for 24h;	99%

p-hydroxyphenethyl alcohol (501-94-0) + tert-butyldimethylsilyl chloride (18162-48-6) → tert-butyl(4-(2-(tert-butyldimethylsilyloxy)ethyl)phenoxy)dimethylsilane (96013-68-2)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 3h;	100%
With 1H-imidazole In N,N-dimethyl-formamide Ambient temperature;	89%
With 1H-imidazole In dichloromethane; N,N-dimethyl-formamide

p-hydroxyphenethyl alcohol (501-94-0) → hydroxytyrosol (10597-60-1)

Conditions	Yield
With polymer-supported IBX In dimethyl carbonate at 20℃; for 1h; chemoselective reaction;	100%
With β-D-glucose; oxygen In aq. phosphate buffer at 37℃; pH=7.0; Enzymatic reaction;	97.5%
Stage #1: p-hydroxyphenethyl alcohol at 20℃; for 1h; Stage #2: With sodium dithionite; water for 0.5h;	90%

p-hydroxyphenethyl alcohol (501-94-0) + epichlorohydrin (106-89-8) → 1-[4-(2-hydroxyethyl)phenoxy]-2,3-epoxypropane (104857-48-9)

Conditions	Yield
With potassium carbonate In toluene; acetonitrile	100%
With potassium carbonate In butanone for 15h; Heating;	86%
Stage #1: p-hydroxyphenethyl alcohol; epichlorohydrin at 80℃; for 1h; Stage #2: With sodium hydroxide at 20℃;	74%

p-hydroxyphenethyl alcohol (501-94-0) + carbonic acid dimethyl ester (616-38-6) → 2-(4'-hydroxyphenyl)ethyl methyl carbonate (953422-33-8)

Conditions	Yield
With sulfuric acid for 7h; Reflux;	100%
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 90℃; for 7.5h;	100%
With Amberlyst 15 for 12h; Reflux;	99%

p-hydroxyphenethyl alcohol (501-94-0) + chloroformic acid ethyl ester (541-41-3) → carbonic acid ethyl ester 4-(2-hydroxy-ethyl)-phenyl ester (1119076-06-0)

Conditions	Yield
With triethylamine In acetonitrile at -80 - 20℃; Inert atmosphere;	100%
With sodium hydroxide In water at -5 - 20℃; for 5h;	92%
With sodium hydroxide at -5 - 50℃; for 5h;	92%
With sodium hydroxide In water at -5 - 20℃; for 6h;	83.3%

p-hydroxyphenethyl alcohol (501-94-0) + carbonic acid dimethyl ester (616-38-6) → 4-methoxyphenethyl methyl carbonate (1796-64-1)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 90℃; for 24h;	100%

vinyl n-butyrate (123-20-6) + p-hydroxyphenethyl alcohol (501-94-0) → 2-(4-hydroxylphenyl)ethyl butyrate (386263-87-2)

Conditions	Yield
With Candida antartica lipase B In tetrahydrofuran at 20℃; for 4h; Enzymatic reaction; chemoselective reaction;	100%
With Novozym 435 at 40℃; for 1h; Enzymatic reaction;

p-hydroxyphenethyl alcohol (501-94-0) + 1-chloro-2-(chloromethyl)benzene (611-19-8) → 2-(4-(2-chlorobenzyloxy)phenyl)ethanol (1228930-61-7)

Conditions	Yield
With potassium carbonate In acetone for 24h; Reflux;	100%

p-hydroxyphenethyl alcohol (501-94-0) + acetic acid (64-19-7) → 2-(4-hydroxyphenyl)ethyl acetate (58556-55-1)

Conditions	Yield
With Candida antarctica at 45℃; for 24h;	100%
With Candida antarctica lipase B at 45℃; for 24h; Enzymatic reaction;	100%
With lipase from Staphylococcus xylosus immobilized onto CaCO3 for 120h; Enzymatic reaction;
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 48h; Inert atmosphere;

p-hydroxyphenethyl alcohol (501-94-0) + propionic acid (802294-64-0) → 2′-(4-hydroxyphenyl)ethylpropanoate

Conditions	Yield
With Candida antarctica at 45℃; for 24h;	100%
With lipase from Staphylococcus xylosus immobilized onto CaCO3 for 120h; Enzymatic reaction;
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 48h; Inert atmosphere;

vinyl pivalate (3377-92-2) + p-hydroxyphenethyl alcohol (501-94-0) → 4-(2-hydroxyethyl)phenyl pivalate (141923-61-7)

Conditions	Yield
With rubidium fluoride In acetonitrile at 80℃; for 3h; regiospecific reaction;	100%

2,2,2-trifluoroethyl acetate (406-95-1) + p-hydroxyphenethyl alcohol (501-94-0) → 2-(4-hydroxyphenyl)ethyl acetate (58556-55-1)

Conditions	Yield
With cesium fluoride In acetonitrile at 80℃; for 24h; Reagent/catalyst;	100%

p-hydroxyphenethyl alcohol (501-94-0) + butyric acid (107-92-6) → 2-(4-hydroxylphenyl)ethyl butyrate (386263-87-2)

Conditions	Yield
With Candida antarctica at 45℃; for 24h;	100%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 24h;

p-hydroxyphenethyl alcohol (501-94-0) + valeric acid (109-52-4) → tyrosol pentanoate

Conditions	Yield
With Candida antarctica at 45℃; for 24h;	100%

p-hydroxyphenethyl alcohol (501-94-0) + butanone (78-93-3) → 2′-(4-hydroxyphenyl)ethylpropanoate

Conditions	Yield
With Candida antarctica lipase B at 45℃; for 24h; Enzymatic reaction;	100%

p-hydroxyphenethyl alcohol (501-94-0) + 2-Pentanone (107-87-9) → 2-(4-hydroxylphenyl)ethyl butyrate (386263-87-2)

Conditions	Yield
With Candida antarctica lipase B at 45℃; for 24h; Enzymatic reaction;	100%

n-hexan-2-one (591-78-6) + p-hydroxyphenethyl alcohol (501-94-0) → tyrosol pentanoate

Conditions	Yield
With Candida antarctica lipase B at 45℃; for 24h; Enzymatic reaction;	100%

p-hydroxyphenethyl alcohol (501-94-0) + benzyl bromide (100-39-0) → 2-(4-benzyloxyphenyl)ethanol (61439-59-6)

Conditions	Yield
With potassium carbonate In acetone for 18h; Heating;	99.3%
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;	98%
With potassium carbonate In acetone Reflux;	98%

p-hydroxyphenethyl alcohol (501-94-0) + acetic anhydride (108-24-7) → 2-(4-acetoxyphenyl)ethyl acetate (60037-42-5)

Conditions	Yield
With pyridine at 20℃; for 24h; Inert atmosphere;	99%
cerium triflate In acetonitrile at 20℃; for 0.2h;	98%
With tributylphosphine at 30℃; for 4h; other reagents: Sc(OTf)3, 4-(dimethylamino)pyridine/pyridine;	95%

p-hydroxyphenethyl alcohol (501-94-0) + benzyl chloride (100-44-7) → 2-(4-benzyloxyphenyl)ethanol (61439-59-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 65℃; for 24h;	99%
Stage #1: p-hydroxyphenethyl alcohol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: benzyl chloride With tetra-(n-butyl)ammonium iodide at 20℃; for 18h;	88%
In ethanol for 9h; Heating;

p-hydroxyphenethyl alcohol (501-94-0) + methyl 2-oxocyclopentane-1-carboxylate (10472-24-9) → 2-oxo-cyclopentanecarboxylic acid 2-(4-hydroxy-phenyl)-ethyl ester

Conditions	Yield
With N,N-3-diethylaminopropylated silica gel In xylene for 3h; Heating;	99%

p-hydroxyphenethyl alcohol (501-94-0) → 4-(2-Hydroxyethyl)cyclohexanol (74058-21-2)

Conditions	Yield
With borax; hydrogen; palladium 10% on activated carbon In isopropyl alcohol at 80℃; under 7500.75 Torr; for 22h;	99%

3-[4-(4-allyloxycarbonylmethylphenoxy)piperidine-1-carbonyl]-1-methyl-3H-imidazol-1-ium iodide + p-hydroxyphenethyl alcohol (501-94-0) → 4-(tert-butyldimethylsilanyloxy)piperidine-1-carboxylic acid 4-(2-hydroxyethyl)phenyl ester

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In dichloromethane at 20℃; for 16h;	99%

p-hydroxyphenethyl alcohol (501-94-0) → 4-hydroxy-phenethyl iodide (6631-69-2)

Conditions	Yield
With chloro-trimethyl-silane; sodium iodide In acetonitrile at 70℃; for 16h;	99%
With chloro-trimethyl-silane; sodium iodide In acetonitrile at 70℃; for 24h; Inert atmosphere;	95%
With 1H-imidazole; iodine; triphenylphosphine In diethyl ether; acetonitrile at 20℃; for 4h;	91%
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 0 - 20℃; Inert atmosphere;	70%
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 20℃; for 4h;

p-hydroxyphenethyl alcohol (501-94-0) + p-nitrophenyl isothiocyanate (2131-61-5) → C15H14N2O4S (1033617-70-7)

Conditions	Yield
Stage #1: p-hydroxyphenethyl alcohol With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: p-nitrophenyl isothiocyanate In tetrahydrofuran at 20℃; for 18h; Further stages.;	99%

p-hydroxyphenethyl alcohol (501-94-0) + 2,2,2-trifluoroethyl benzoate (1579-72-2) → 2-(4-hydroxyphenyl)ethyl benzoate

Conditions	Yield
With (μ-oxo)bis[(1,2-ethanediamino-N,N'-bis(salicylidene))iron(III)] In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 24h; Inert atmosphere; Schlenk technique; chemoselective reaction;	99%

p-hydroxyphenethyl alcohol (501-94-0) + ethyl acetate (141-78-6) → 2-(4-hydroxyphenyl)ethyl acetate (58556-55-1)

Conditions	Yield
With sodium hydrogen sulfate In hexane for 26h; Heating;	98%
With sodium hydrogen sulfate; silica gel In hexane Heating;	98%
With toluene-4-sulfonic acid at 80℃; for 5h; Reagent/catalyst; Temperature;	98.9%

p-hydroxyphenethyl alcohol (501-94-0) + perfluoro(4-methyl-3-isopropyl-2-pentene) (30320-27-5) → 4-(perfluoro(4-methyl-3-isopropyl-2-penten-2-yl))oxyphenylethanol

Conditions	Yield
With potassium carbonate In tetrahydrofuran for 4h; Inert atmosphere; Reflux;	98.6%

Upstream product

• 94414-03-6 4-[2-(acetyloxy)ethyl]-4-hydroxy-2,5-cyclohexadien-1-one 
• 836-42-0 4-benzyloxybenzyl chloride 
• 35897-92-8 ligstroside 
• 67-56-1 methanol 
• 97549-57-0 osmanthuside B 
• 156-38-7 4-hydroxyphenylacetate 
• 60-18-4 L-tyrosine 
• 539-15-1 N,N-dimethyltyramine 
• 28145-35-9 4-(2-chloroethyl)phenol 
• 6631-69-2 4-hydroxy-phenethyl iodide 
• 51-67-2 tyrosamine 
• 142998-21-8 fraxiformoside 
• 156-39-8 4-hydroxyphenylpiruvic acid 
• 2628-17-3 4-Vinylphenol 

Downstream Products

• 58556-55-1 2-(4-hydroxyphenyl)ethyl acetate 
• 141923-61-7 4-(2-hydroxyethyl)phenyl pivalate 
• 141923-60-6 2-(4-hydroxyphenyl)ethyl pivalate 
• 10597-60-1 hydroxytyrosol 
• 76221-87-9 1-(p-tolylsulfonyl)-2-(4-hydroxyphenyl)ethane 
• 197510-39-7 4-(2-quinolylmethoxy)phenethyl alcohol 
• 110005-81-7 2-hydroxy-5-(2-hydroxyethyl)-benzaldehyde 
• 93721-28-9 2-{4-[2-(diethylamino)ethoxy]-phenyl}-ethanol 
• 1026621-36-2 4-Hexyloxy-3,5-dimethoxy-benzoic acid 4-(2-hydroxy-ethyl)-phenyl ester 
• 96013-68-2 tert-butyl(4-(2-(tert-butyldimethylsilyloxy)ethyl)phenoxy)dimethylsilane 
• 28251-63-0 tetraacetyl salidroside 
• 60037-42-5 2-(4-acetoxyphenyl)ethyl acetate 
• 98704-58-6 2-(4-(allyloxy)phenyl)ethanol 
• 140893-10-3 ethyl 2-[4-(2-hydroxyethyl)phenoxy]acetate 

Relevant articles and documents

Rapid biosynthesis of phenolic glycosides and their derivatives from biomass-derived hydroxycinnamates

Biomass-derived hydroxycinnamates (mainly includingp-coumaric acid and ferulic acid), which are natural sources of aromatic compounds, are highly underutilized resources. There is a need to upgrade them to make them economically feasible. Value-added phenolic glycosides and their derivatives, both belonging to a class of plant aromatic natural products, are widely used in the nutraceutical, pharmaceutical, and cosmetic industries. However, their complex aromatic structures make their efficient biosynthesis a challenging process. To overcome this issue, we created three novel synthetic cascades for the biosynthesis of phenolic glycosides (gastrodin, arbutin, and salidroside) and their derivatives (hydroquinone, tyrosol, hydroxytyrosol, and homovanillyl alcohol) fromp-coumaric acid and ferulic acid. Moreover, because the biomass-derived hydroxycinnamates directly provided aromatic units, the cascades enabled efficient biosynthesis. We achieved substantially high production rates (up to or above 100-fold enhancement) relative to the glucose-based biosynthesis. Given the ubiquity of the aromatic structure in natural products, the use of biomass-derived aromatics should facilitate the rapid biosynthesis of numerous aromatic natural products.

An Aldehyde Responsive, Cleavable Linker for Glucose Responsive Insulins

A glucose responsive insulin (GRI) that responds to changes in blood glucose concentrations has remained an elusive goal. Here we describe the development of glucose cleavable linkers based on hydrazone and thiazolidine structures. We developed linkers with low levels of spontaneous hydrolysis but increased level of hydrolysis with rising concentrations of glucose, which demonstrated their glucose responsiveness in vitro. Lipidated hydrazones and thiazolidines were conjugated to the LysB29 side-chain of HI by pH-controlled acylations providing GRIs with glucose responsiveness confirmed in vitro for thiazolidines. Clamp studies showed increased glucose infusion at hyperglycemic conditions for one GRI indicative of a true glucose response. The glucose responsive cleavable linker in these GRIs allow changes in glucose levels to drive the release of active insulin from a circulating depot. We have demonstrated an unprecedented, chemically responsive linker concept for biopharmaceuticals.

Efficient Synthesis of Phenylacetate and 2-Phenylethanol by Modular Cascade Biocatalysis

The green and sustainable synthesis of chemicals from renewable feedstocks by a biotransformation approach has gained increasing attention in recent years. In this work, we developed enzymatic cascades to efficiently convert l-phenylalanine into 2-phenylethanol (2-PE) and phenylacetic acid (PAA), l-tyrosine into tyrosol (p-hydroxyphenylethanol, p-HPE) and p-hydroxyphenylacetic acid (p-HPAA). The enzymatic cascade was cast into an aromatic aldehyde formation module, followed by an aldehyde reduction module, or aldehyde oxidation module, to achieve one-pot biotransformation by using recombinant Escherichia coli. Biotransformation of 50 mM l-Phe produced 6.76 g/L PAA with more than 99 % conversion and 5.95 g/L of 2-PE with 97 % conversion. The bioconversion efficiencies of p-HPAA and p-HPE from l-Tyr reached to 88 and 94 %, respectively. In addition, m-fluoro-phenylalanine was further employed as an unnatural aromatic amino acid substrate to obtain m-fluoro-phenylacetic acid; '96 % conversion was achieved. Our results thus demonstrated high-yielding and potential industrial synthesis of above aromatic compounds by one-pot cascade biocatalysis.