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trans-4-Hydroxycinnamic acid

trans-4-Hydroxycinnamic acid structure

CAS No:
501-98-4
Formula:
C9H8O3
Chemical Name:
trans-4-Hydroxycinnamic acid
Synonyms:
2-Propenoic acid,3-(4-hydroxyphenyl)-,(2E)-;Cinnamic acid,p-hydroxy-,(E)-;2-Propenoic acid,3-(4-hydroxyphenyl)-,(E)-;(2E)-3-(4-Hydroxyphenyl)-2-propenoic acid;Naringeninic acid;trans-p-Coumaric acid;(E)-p-Coumaric acid;trans-p-Hydroxycinnamic acid;(E)-p-Hydroxycinnamic acid;trans-4-Hydroxycinnamic acid;p-Hydroxy-trans-cinnamic acid;(E)-3-(4-Hydroxyphenyl)-2-propenoic acid;trans-4-Coumaric acid;p-trans-Coumaric acid;(E)-4-Hydroxycinnamic acid;trans-3-(4-Hydroxyphenyl)-2-propenoic acid;(E)-3-(4-Hydroxyphenyl)acrylic acid;trans-p-Coumarinic acid;(2E)-3-(4-Hydroxyphenyl)prop-2-enoic acid;(E)-3-(4-Hydroxyphenyl)acrylic acid
Categories:
Agrochemicals > Insecticides

Description

p-Coumaric acid is the abundant isomer of cinnamic acid which has antitumor and anti-mutagenic activities.

Solid

4-coumaric acid is a coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring. It has a role as a plant metabolite. It is a conjugate acid of a 4-coumarate.

trans-4-Hydroxycinnamic acid Basic Attributes

Molecular Weight：

164.16

Exact Mass：

164.16

BRN：

2207383

EC Number：

231-000-0

UNII：

IBS9D1EU3J

NSC Number：

674321|59260

DSSTox ID：

DTXSID6064660

HScode：

2918290000

Characteristics

PSA：

57.5

XLogP3：

1.5

Appearance：

Off-white to beige or greenish Powder

Density：

1.3±0.1 g/cm3

Melting Point：

214 °C (decomp)

Boiling Point：

329.3°C at 760 mmHg

Flash Point：

177.3±17.4 °C

Refractive Index：

1.660

Water Solubility：

H2O: soluble ;ethanol: soluble 50mg/mL

Storage Conditions：

Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

Collision Cross Section：

127 Å² [M+H-H2O]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|129.27 Å² [M-H]- [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|131.1 Å² [M-H]- [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|131.3 Å² [M-H]-

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38

safety instructions：

26-36-37/39

RTECS Number：

GD9095000

Marks：

Stability/Shelf Life：

Stable at room temperature in closed containers under normal storage and handling conditions.

Precautionary statement(s)：

P305 + P351 + P338

Hazard Statements：

H315-H319-H335

GHS Classification：

|Danger|H301 (18.75%): Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P271, P272, P280, P301+P310, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P332+P313, P333+P313, P337+P313, P361, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 16 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 108 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH：

Chemical substances or agents with contraceptive activity in males. Use for male contraceptive agents in general or for which there is no specific heading. (See all compounds classified as Contraceptive Agents, Male.)|Substances that eliminate free radicals. Among other effects, they protect PANCREATIC ISLETS against damage by CYTOKINES and prevent myocardial and pulmonary REPERFUSION INJURY. (See all compounds classified as Free Radical Scavengers.)|Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)|Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)

MeSH Entry Terms：

4-coumaric acid

trans-4-Hydroxycinnamic acid Use and Manufacturing

Methods of Manufacturing

The preparation method is based on acetylsalicyloyl chloride as raw material, reacts with diethyl malonate in acetonitrile solvent in the presence of magnesium chloride, then adds triethylamine, and reacts at 0°C for 1h to obtain (2-acetoxybenzene Formyl) diethyl malonate product, then heated to 50 ℃ in potassium hydroxide/methanol solution, reacted for 3h, cyclized to obtain the product. You can also use ethyl acetoacetate as a raw material, in the presence of sodium hydroxide, in isobutyl methyl ketone solvent with acetylsalicyloyl chloride at 15 ~ 20 ℃ for 3.5 h to obtain 2- (2-hydroxybenzoyl) acetyl Acetic acid sodium salt, the reaction product is reacted with hydrochloric acid at 25-30°C for 30 min to obtain 3-acetyl-4-hydroxycoumarin, and then heated under concentrated sulfuric acid at 90-95°C for 4h to obtain the product. You can also use 2-hydroxyacetophenone as a raw material, in the presence of potassium carbonate, in the autoclave through 5.88MPa carbon dioxide, at room temperature for 15h, and then maintained at 60 ℃ for 15h, first generate 2-hydroxybenzene-3- Oxypropionic acid, then cyclic synthesis products.

Uses

trans-p-Coumaric Acid is the E-isomer of p-Coumaric Acid (C755365), a hydroxy derivative of Cinnamic Acid with antioxidant properties. p-Coumaric acid is a is a major component of lignocellulose. Studies suggest that p-Coumaric Acid may reduce the risk of cancer by reducing the formation of carcinogenic nitrosamines.

Manufacturing Info：

2-Propenoic acid, 3-(4-hydroxyphenyl)-: ACTIVE

Use Classification：

Cosmetics -> Skin conditioning

Computed Properties

Molecular Weight:164.16
XLogP3:1.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:164.047344113
Monoisotopic Mass:164.047344113
Topological Polar Surface Area:57.5
Heavy Atom Count:12
Complexity:178
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Phenol

Potassium hydroxide

Ethyl acetate

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Guide of trans-4-Hydroxycinnamic acid

Description
Basic Attributes
Characteristics
Safety Information
Drug Information
Use and Manufacturing
Computed Properties
Material
Recommended Suppliers
Latest News
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