3-Hydroxy-4-methoxycinnamic acid
- Product Name
- 3-Hydroxy-4-methoxycinnamic acid
- CAS No.
- 537-73-5
- Chemical Name
- 3-Hydroxy-4-methoxycinnamic acid
- Synonyms
- ISOFERULIC ACID;(E)-3-(3-hydroxy-4-Methoxyphenyl)acrylic acid;Isoferulic;HESPERETIC ACID;Hesperetate;Isoferulate;Isoferulic Aci;HESPERETINIC ACID;AKOS BBS-00006960;Hesperitinic acid
- CBNumber
- CB9178579
- Molecular Formula
- C10H10O4
- Formula Weight
- 194.18
- MOL File
- 537-73-5.mol
3-Hydroxy-4-methoxycinnamic acid Property
- Melting point:
- 230 °C (dec.)(lit.)
- Boiling point:
- 250.62°C (rough estimate)
- Density
- 1.0583 (rough estimate)
- refractive index
- 1.5168 (estimate)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- Soluble in ethanol and methanol.
- pka
- 4.53±0.10(Predicted)
- form
- Solid
- color
- Pale Yellow
- BRN
- 2212760
- InChI
- InChI=1S/C10H10O4/c1-14-9-4-2-7(6-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)
- InChIKey
- QURCVMIEKCOAJU-UHFFFAOYSA-N
- SMILES
- C(O)(=O)C=CC1=CC=C(OC)C(O)=C1
- LogP
- 0.788 (est)
- CAS DataBase Reference
- 537-73-5(CAS DataBase Reference)
- NIST Chemistry Reference
- Cinnamic acid, 3-hydroxy-4-methoxy-(537-73-5)
Safety
- Hazard Codes
- Xi
- Risk Statements
- 36/37/38
- Safety Statements
- 26-37/39-24/25
- WGK Germany
- 2
- RTECS
- UD3365400
- Hazard Note
- Irritant
- HS Code
- 29189090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405Store locked up.
N-Bromosuccinimide Price
- Product number
- 103012
- Product name
- 3-Hydroxy-4-methoxycinnamic acid, predominantly trans
- Purity
- 97%
- Packaging
- 1g
- Price
- $21.4
- Updated
- 2025/07/31
- Product number
- 103012
- Product name
- 3-Hydroxy-4-methoxycinnamic acid, predominantly trans
- Purity
- 97%
- Packaging
- 5g
- Price
- $204
- Updated
- 2025/07/31
- Product number
- H0524
- Product name
- 3-Hydroxy-4-methoxycinnamic Acid
- Purity
- >98.0%(T)(HPLC)
- Packaging
- 1g
- Price
- $56
- Updated
- 2025/07/31
- Product number
- H0524
- Product name
- 3-Hydroxy-4-methoxycinnamic Acid
- Purity
- >98.0%(T)(HPLC)
- Packaging
- 5g
- Price
- $220
- Updated
- 2025/07/31
- Product number
- 22715
- Product name
- Isoferulic Acid
- Purity
- ≥98%
- Packaging
- 1g
- Price
- $32
- Updated
- 2024/03/01
3-Hydroxy-4-methoxycinnamic acid Chemical Properties,Usage,Production
Chemical Properties
Off-White Crystalline Solid
Uses
3-Hydroxy-4-methoxycinnamic Acid (Isoferulic acid) is a hypoglycemic agent.
Uses
3-Hydroxy-4-methoxycinnamic acid exhibits hypoglycemic properties.
Uses
3-Hydroxy-4-methoxycinnamic acid was used in the synthesis of tranilast and various tranilast analogs (cinnamoyl anthranilates) by genetically engineered Saccharomyces cerevisiae yeast strain. It was also used in the synthesis of glycoside compounds by undergoing glycosidation.
Definition
ChEBI: A ferulic acid consisting of trans-cinnamic acid bearing methoxy and hydroxy substituents at positions 4 and 3 respectively on the phenyl ring.
General Description
3-Hydroxy-4-methoxycinnamic acid, predominantly trans is available as white crystals. 3-Hydroxy-4-methoxycinnamic acid is isolated from the aerial part of Artemisia capillaris, Chinese medicinal plant. It is a component of chinese herbal medicine used for a pain killer and stomachic. It is an efficient acetylcholine inhibitor. 3-Hydroxy-4-methoxycinnamic acid is bioactive metabolite of Spilanthes acmella Murr. It increases the resistance of low-density lipoprotein (LDL) to oxidation.
Synthesis
621-59-0
141-82-2
537-73-5
To a suspension of isovanillin (152 mg, 1.00 mmol) and malonic acid (416 mg, 4.00 mmol) in toluene (5 mL) was added triethylamine (0.70 mL, 5.00 mmol) and N,N-dimethylformamide dimethyl acetal (0.20 mL, 1.50 mmol). The reaction mixture was heated to reflux for 4 hours, subsequently cooled to room temperature and concentrated on a rotary evaporator. The residue was dissolved in 1 M NaOH solution (20 mL) and the resulting solution was washed with dichloromethane (3 x 20 mL). The aqueous phase was acidified to pH 1 by the addition of 3 M HCl. The milky precipitate formed was collected in a Hirsch funnel, washed with dilute hydrochloric acid and air dried. The precipitate was recrystallized by solvent recrystallization in a methanol-water mixture and dried in a vacuum desiccator using phosphorus pentoxide as a drying agent to give trans-3-hydroxy-4-methoxycinnamic acid (164 mg, 85% yield) as a cream-colored crystalline solid.1H NMR spectroscopic data were in agreement with those reported in the literature (McCorkindale, N.J.; McCulloch, A.W. Magrill, D.S.; Caddy, B.; Martin-Smith, M.; Smith, S.J.; Stenlake, J.B. Tetrahedron 1969, 25, 5475).
IC 50
α adrenergic receptor
References
[1] Synthetic Communications, 1995, vol. 25, # 20, p. 3187 - 3197
[2] Chemical Communications, 1998, # 21, p. 2335 - 2336
[3] Tetrahedron, 2007, vol. 63, # 4, p. 960 - 965
[4] Tetrahedron Letters, 2012, vol. 53, # 20, p. 2537 - 2539
[5] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 9, p. 2707 - 2713
3-Hydroxy-4-methoxycinnamic acid Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 3-Hydroxy-4-methoxycinnamic acid manufacturers
- Product
- 3-Hydroxy-4-methoxycinnamic acid 537-73-5
- Price
- US $456.00-440.00/kilograms
- Min. Order
- 10kilograms
- Purity
- 99%
- Supply Ability
- 100tons
- Release date
- 2023-02-16
- Product
- 3-Hydroxy-4-methoxycinnamic acid 537-73-5
- Price
- US $100.00/bag
- Min. Order
- 1bag
- Purity
- 99
- Supply Ability
- 5000
- Release date
- 2023-09-14
- Product
- 3-Hydroxy-4-methoxycinnamic acid 537-73-5
- Price
- US $10.00/kg
- Min. Order
- 1kg
- Purity
- 99.99%
- Supply Ability
- 50000tons
- Release date
- 2023-07-10