3-(4-Hydroxy-3-Methoxyphenyl)Prop-2-Enoic Acid

HCID 709CAS 1135-24-6

Basic information

Standard SMILES
COc1cc(C=CC(=O)O)ccc1O
InChIKey
KSEBMYQBYZTDHS-UHFFFAOYSA-N
Molecular formula
C10H10O4
Average molar mass
194.18 g/mol
Monoisotopic mass
194.0579088

Overview

(E/Z)-ferulic acid has been reported in Camellia reticulata, Angelica gigas, and other organisms with data available.

Names & identifiers

Preferred name
3-(4-Hydroxy-3-Methoxyphenyl)Prop-2-Enoic Acid
IUPAC
3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid
English name
Ferulic Acid
Molecular formula
C10H10O4
Molecular weight
194.18

Names & synonyms

3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acidRefChem:1066861(E/Z)-ferulic acid(2E)-3-(4-Hydroxy-3-methoxyphenyl)acrylic acidTrans-3-(4-hydroxy-3-methoxyphenyl)acrylic acid3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoic acidferulic acid (trans-4-hydroxy-3-methoxycinnamic acid)EINECS 214-490-0CIS-FERULICACIDbmse000587DTXSID70892035ferulasaur
Show more names
Ferulate4-HYDROXY-3-METHOXYCINNAMIC ACIDFerulic3-METHOXY-4-HYDROXYCINNAMIC ACIDFERULLIC ACIDferulaic aciderulic AcidForulic acidFERULIC ACID pureTIMTEC-BB SBB000326
4-Hydroxy-3-methoxy cinnamic acidBBL010345AC-7965Ferulic acid CRStrans-Ferulic Acid (purified by sublimation)Spectrum_001256SpecPlus_000547Spectrum2_001394

Database identifiers

CAS
1135-24-6
PubChem CID
709
DTXSID
DTXSID5040673
ChEMBL
CHEMBL3185646

Properties

Computed structural properties

XLogP
1.5
Topological polar surface area
66.8 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
4
Rotatable bonds
3
Heavy atoms
14

Experimental & physicochemical properties

LogP1.87

Physicochemical properties

Melting point
168 · 168-172 °C(lit.)
Boiling point
250.62 °C · 250.62°C (rough estimate)
Density
1.316 · 1.316(20.0000℃)
vapor pressure
0 Pa · 0Pa at 25℃
refractive index
1.5168 · 1.5168 (estimate)
FLAVIS Number
8.089 · 08.089 | 4-Hydroxy-3-methoxycinnamic acid (mixture of isomers)

Safety & regulation

Safety data

wgk
3
tsca
TSCA listed
rtecs
UD3365500
hs_code
29162090
Toxicity
mouse,LD,intraperitoneal,> 350mg/kg (350mg/kg),BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)BEHAVIORAL: ATAXIABEHAVIORAL: REGIDITY,Indian Journal of Pharmaceutical Sciences. Vol. 49, Pg. 77, 1987.
risk_code
36/37/38

Chemistry & industry

Applications · 8 items

HistoryFerulic acid is a derivative of cinnamic acid with molecular formula C10H10O4. In 1886, Hlasiwetz Barth, an Austrian, isolated 3-methoxy-4-hydroxycinnamic acid from the genus Ferula foetida for structure determination. Ferulic acid together with dihydroferulic acid, is a component of lignocelluloses, conferring cell wall rigidity by cross linking lignin and polysaccharides. It is commonly found in seeds of plant such as rice, wheat and oats. Besides, Ferulic Acid exhibited biochemical role in the inhibition of seed germination, inhibition of indole-acetic acid and enzyme, inhibition of decarboxylation activity & other protective effect on micro-organisms and pets. The syntheis of Ferulic acid was established by Dutt in 1935 when ferulic acid was used as a precursor in the manufacturing of vanillin and malonic acid. There are vast numbers of studies documented on the bio-medical properties of ferulic acid such as antioxidant activity, UV-absorbing capacity & its effect of lignin as precursor in plants metabolic pathway. Ferulic acid, being highly abundant, is indeed difficult to synthesize, Oryza Oil & Fat Chemical has successfully developed an efficient method to extract ferulic acid from rice bran and suitable for applications in the health and beauty arena.

UsesIt can be used as a food preservative and a kind of organic chemicals. It can be used as the intermediates of cinametic acid. It can also be used as food preservative. It can also be applied to biochemical studies

DescriptionFerulic acid is widely found in plants, especially in artichoke, eggplant and corn bran. In addition, it is also present in a variety of Chinese herbal medicines, such as angelica, dome, motherwort, snow ganoderma lucidum and so on.

HistoryFerulic acid was first isolated from the medicinal plants ferulic in 1866. The biologi_x005fcal activity of ferulic acid was not revealed until 1957 when the pioneering study of Preziosi P in Italy showed for the first time the efficacy of ferulic acid in regulating blood lipids and diuretic . In 1979, Lin Mao and others isolated ferulic acid from the Chinese medicine angelica and reported that ferulic acid had the inhibitory effect on platelet aggregation . Since then, more and more medicinal efficacy of ferulic acid has gradually been recognized.

UsesWidely distributed in small amounts in plants. Used as an antioxidant and food preservative

Usesantineoplastic, choleretic, food preservative

Usesanti-oxidant, anti-inflammatory, sunscreen enhancer

Usesferulic acid is a plant-derived anti-oxidant and free-radical scavenger, it protects the skin against uVB-induced redness. When incorporated into formulas with ascorbic acid and tocopherol, ferulic acid can improve their stability and double the photoprotection capacities offered by the formulation. In clinical studies, ferulic acid exhibits good permeation capacities through the stratum corneum, which can be attributed to its lipophilic properties.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
西安天朗源生物科技有限公司17749038280 17749038280 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]

Additional notes

DefinitionA plant growth inhibitor.

Related reactions

19 records

Linked notes

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