Related Searches: 3,4-Dihydroxycinnamic acid, 3,4-Pyridinedicarboxylic acid, 3,4-Difluorobenzoic acid, 3,4-Difluorophenylboronic acid, 3,4-Dimethoxybenzoic acid, View all

3,4-Dihydroxycinnamic acid(CAS No. 331-39-5)

3,4-Dihydroxycinnamic acid C9H8O4 (cas 331-39-5) Molecular Structure

331-39-5 Structure

Identification and Related Records

【Name】
3,4-Dihydroxycinnamic acid
【CAS Registry number】
331-39-5
【Synonyms】
Caffeicacid,96%
Caffeic acid
【EINECS(EC#)】
206-361-2
【Molecular Formula】
C9H8O4 (Products with the same molecular formula)
【Molecular Weight】
180.16
【Inchi】
InChI=1/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+
【InChIKey】
QAIPRVGONGVQAS-DUXPYHPUSA-N
【Canonical SMILES】
C1=CC(=C(C=C1C=CC(=O)O)O)O
【Isomers smiles】
C1=CC(=C(C=C1/C=C/C(=O)O)O)O
【MOL File】
331-39-5.mol

Chemical and Physical Properties

【Appearance】
Light yellow to greenish-yellow powder
【Density】
1.478 g/cm3
【Melting Point】
194-198℃ (dec.)
【Boiling Point】
416.8 °C at 760 mmHg
【Flash Point】
220 °C
【Water】
soluble in hot water
【Solubilities】
soluble in hot water
【Color/Form】
yellow to tan
【Stability】
Stable. Combustible. Incompatible with strong oxidizing agents, strong bases.
【HS Code】
29182990
【Storage temp】
Store at RT.
【Spectral properties】
Observed light absorption wavelengths = 265 nm, 325 nm, and 442 nm.
【Computed Properties】
Molecular Weight:180.15742 [g/mol]
Molecular Formula:C9H8O4
XLogP3:1.2
H-Bond Donor:3
H-Bond Acceptor:4
Rotatable Bond Count:2
Tautomer Count:16
Exact Mass:180.042259
MonoIsotopic Mass:180.042259
Topological Polar Surface Area:77.8
Heavy Atom Count:13
Formal Charge:0
Complexity:212
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:1
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Donor Count:2
Feature 3D Anion Count:1
Feature 3D Ring Count:1
Effective Rotor Count:2
Conformer Sampling RMSD:0.6
CID Conformer Count:2

Safety and Handling

【Hazard Codes】
Xn:Harmful
【Risk Statements】
R36/37/38;R40
【Safety Statements 】
S26;S36/37/39
【Hazard Note】

Irritant

【Safety】

Moderately toxic by intraperitoneal route. An experimental teratogen. Mutation data reported. When heated to decomposition it emits acrid smoke and fumes.
Hazard Codes:?HarmfulXn,IrritantXi
Risk Statements: 36/37/38-40-63-68
R36/37/38:Irritating to eyes, respiratory system and skin.?
R40:Limited evidence of a carcinogenic effect.?
R63:Possible risk of harm to the unborn child.?
R68:Possible risk of irreversible effects.
Safety Statements: 26-36/37/39-36?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.?
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.

【Cleanup Methods】
PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/
【Transport】
25kgs
【Other Preventative Measures】
PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... Clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Vertical laminar-flow biological safety cabinets may be used for containment of in vitro procedures ... provided that the exhaust air flow is sufficient to provide an inward air flow at the face opening of the cabinet, & contaminated air plenums that are under positive pressure are leak-tight. Horizontal laminar-flow hoods or safety cabinets, where filtered air is blown across the working area towards the operator, should never be used ... Each cabinet or fume cupboard to be used ... should be tested before work is begun (eg, with fume bomb) & label fixed to it, giving date of test & avg air-flow measured. This test should be repeated periodically & after any structural changes. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Principles that apply to chem or biochem lab also apply to microbiological & cell-culture labs ... Special consideration should be given to route of admin. ... Safest method of administering volatile carcinogen is by injection of a soln. Admin by topical application, gavage, or intratracheal instillation should be performed under hood. If chem will be exhaled, animals should be kept under hood during this period. Inhalation exposure requires special equipment. ... Unless specifically required, routes of admin other than in the diet should be used. Mixing of carcinogen in diet should be carried out in sealed mixers under fume hood, from which the exhaust is fitted with an efficient particulate filter. Techniques for cleaning mixer & hood should be devised before expt begun. When mixing diets, special protective clothing &, possibly, respirators may be required. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": When ... admin in diet or applied to skin, animals should be kept in cages with solid bottoms & sides & fitted with a filter top. When volatile carcinogens are given, filter tops should not be used. Cages which have been used to house animals that received carcinogens should be decontaminated. Cage-cleaning facilities should be installed in area in which carcinogens are being used, to avoid moving of ... contaminated /cages/. It is difficult to ensure that cages are decontaminated, & monitoring methods are necessary. Situations may exist in which the use of disposable cages should be recommended, depending on type & amt of carcinogen & efficiency with which it can be removed. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": To eliminate risk that ... contamination in lab could build up during conduct of expt, periodic checks should be carried out on lab atmospheres, surfaces, such as walls, floors & benches, & ... interior of fume hoods & airducts. As well as regular monitoring, check must be carried out after cleaning-up of spillage. Sensitive methods are required when testing lab atmospheres. ... Methods ... should ... where possible, be simple & sensitive. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Rooms in which obvious contamination has occurred, such as spillage, should be decontaminated by lab personnel engaged in expt. Design of expt should ... avoid contamination of permanent equipment. ... Procedures should ensure that maintenance workers are not exposed to carcinogens. ... Particular care should be taken to avoid contamination of drains or ventilation ducts. In cleaning labs, procedures should be used which do not produce aerosols or dispersal of dust, ie, wet mop or vacuum cleaner equipped with high-efficiency particulate filter on exhaust, which are avail commercially, should be used. Sweeping, brushing & use of dry dusters or mops should be prohibited. Grossly contaminated cleaning materials should not be re-used ... If gowns or towels are contaminated, they should not be sent to laundry, but ... decontaminated or burnt, to avoid any hazard to laundry personnel. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Doors leading into areas where carcinogens are used ... should be marked distinctively with appropriate labels. Access ... limited to persons involved in expt. ... A prominently displayed notice should give the name of the Scientific Investigator or other person who can advise in an emergency & who can inform others (such as firemen) on the handling of carcinogenic substances. /Chemical Carcinogens/
【Specification】

?Caffeic acid , its cas register number is 331-39-5. It also can be called 3,4-Dihydroxycinnamic acid ; 3,4-Dihydroxybenzeneacrylic acid ; and 3-(3,4-Dihydroxy phenyl)-2-propenoic acid .?It is a naturally occurring organic compound, and?is found in all plants because it is a key intermediate in the biosynthesis of lignin. It is hazardous, so the first aid measures and others should be known. Such as: When on the skin: first, should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly, get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While, it's inhaled: Remove from exposure and move to fresh air immediately. Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product:?Wash mouth out with water, and get medical aid immediately.
In addition, Caffeic acid (CAS NO.331-39-5) could be stable under normal temperatures and pressures. It is not compatible with strong oxidizing agents, strong acids, strong bases, and you must not take it with incompatible materials. And also prevent it to broken down into hazardous decomposition products:?Carbon monoxide, carbon dioxide.

【Octanol/Water Partition Coefficient】
log Kow = 1.15
【Disposal Methods】
PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": ... Small quantities of ... some carcinogens can be destroyed using chem reactions ... but no general rules can be given. ... As a general technique ... treatment with sodium dichromate in strong sulfuric acid can be used. The time necessary for destruction ... is seldom known ... but 1-2 days is generally considered sufficient when freshly prepd reagent is used. ... Carcinogens that are easily oxidizable can be destroyed with milder oxidative agents, such as saturated soln of potassium permanganate in acetone, which appears to be a suitable agent for destruction of hydrazines or of compounds containing isolated carbon-carbon double bonds. Concn or 50% aqueous sodium hypochlorite can also be used as an oxidizing agent. /Chemical Carcinogens/
PRECAUTIONS FOR "CARCINOGENS": Carcinogens that are alkylating, arylating or acylating agents per se can be destroyed by reaction with appropriate nucleophiles, such as water, hydroxyl ions, ammonia, thiols & thiosulfate. The reactivity of various alkylating agents varies greatly ... & is also influenced by sol of agent in the reaction medium. To facilitate the complete reaction, it is suggested that the agents be dissolved in ethanol or similar solvents. ... No method should be applied ... until it has been thoroughly tested for its effectiveness & safety on material to be inactivated. For example, in case of destruction of alkylating agents, it is possible to detect residual compounds by reaction with 4(4-nitrobenzyl)-pyridine. /Chemical Carcinogens/

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Constituent of plants, probably occurs in plants only in conjugated forms, e.g., chlorogenic acid.
Isolation from green coffee: Wolfrom et al., J. Agr. Food Chem. 8, 58 (1960); from roasted coffee: Krasemann, Arch. Pharm. 293, 721 (1960). Formation by acid hydrolysis of chlorogenic acid: Fiedler, Arzneimittel-Forsch. 4, 41 (1954); Whiting, Carr, Nature 180, 1479 (1957); Guern, C.A. 61, 9965h (1964).
【Usage】

Constituent of plants, probably occurs in plants only in conjugated forms.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Naturally occurring or synthetic substances that inhibit or retard the oxidation of a substance to which it is added. They counteract the harmful and damaging effects of oxidation in animal tissues.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 100(SRC), determined from a log Kow of 1.15(2) and a regression-derived equation(3), indicates that caffeic acid is expected to have high mobility in soil(SRC). Volatilization of caffeic acid from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.4X10-16 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Caffeic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.5X10-7 mm Hg(SRC), determined from a fragment constant method(5). C-14 ring-labeled caffeic acid underwent approximately 55 percent mineralization after two weeks in a sandy loam mixed culture(6).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 100(SRC), determined from a log Kow of 1.15(2) and a regression-derived equation(3), indicates that caffeic acid is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.4X10-16 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). The pKa of caffeic acid is 4.62(5), indicating that this compound will primarily exist in anion form in the environment and anions generally do not adsorb to organic carbon and clay more strongly than their neutral counterparts(6). Caffeic acid is degraded in natural sunlit waters by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in water is 11 days(SRC) at an aquatic hydroxyl radical concentration of 3X10-17 M(7), calculated from its rate constant of 2.41X10+10 per M-sec at 25 deg C(8). According to a classification scheme(9), an estimated BCF of 3.2(SRC), from its log Kow(2) and a regression- derived equation(10), suggests the potential for bioconcentration in aquatic organisms is low(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), caffeic acid, which has an estimated vapor pressure of 2.5X10-7 mm Hg at 25 deg C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase caffeic acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 8.6 hrs(SRC), calculated from its rate constant of 4.5X10-11 cu cm/molecule-sec at 25 deg C(SRC) that was derived using a structure estimation method(3). Caffeic acid has been shown to absorb light at 325 nm and 442 nm, indicating the potential for direct photolysis(4).

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