Cinnamic acid

Modify Date: 2024-01-02 17:18:03

Cinnamic acid Structure
Cinnamic acid structure
Common Name Cinnamic acid
CAS Number 621-82-9 Molecular Weight 148.159
Density 1.2±0.1 g/cm3 Boiling Point 265.0±0.0 °C at 760 mmHg
Molecular Formula C9H8O2 Melting Point 133ºC
MSDS N/A Flash Point 189.5±9.6 °C

 Use of Cinnamic acid


Cinnamic acid has potential use in cancer intervention, with IC50s of 1-4.5 mM in glioblastoma, melanoma, prostate and lung carcinoma cells.

 Names

Name cinnamic acid
Synonym More Synonyms

 Cinnamic acid Biological Activity

Description Cinnamic acid has potential use in cancer intervention, with IC50s of 1-4.5 mM in glioblastoma, melanoma, prostate and lung carcinoma cells.
Related Catalog
Target

Human Endogenous Metabolite

In Vitro Treatment with Cinnamic acid (CINN) of various tumor cells of epithelial and neuroectodermal origin result in dose-dependent growth inhibition following a 3-day exposure. The inhibitory concentrations causing a 50% reduction in tumor-cell proliferation (IC50) are between 1.2 to 4.5 mM. It is also showed that 20 mM Cinnamic acid is needed to cause an IC50 in FS4 cells, i.e. 5 to 20 times more than for tumor cells. In addition to inhibiting tumor-cell proliferation, Cinnamic acid causes morphological changes consistent with melanocyte differentiation. Within 5 days of treatment with 5 mM Cinnamic acid, melanoma 1011 cells appear enlarged with a markedly increased cytoplasm-to-nuclear ratio and well organized cytoskeleton, developed long dendritic processes and became highly melanotic. The change in the capacity of Cinnamic acid -treated melanoma 1011, A375(M) and SKMEL28 cells to degrade and cross tissue barriers is assessed by an in vitro invasion assay using modified Boyden chambers with matrigel-coated filters. After 3 days of continuous treatment with Cinnamic acid, a dose-dependent loss of invasive capacity in 3 tested tumor lines is observed. Treatment with 5 mM Cinnamic acid results in 75-95% loss of invasiveness[1].
Cell Assay The cell lines used, established from human malignant tumors, are A549 (lung cancer); PC3(M), Du145, and LNCaP (prostate cancer); A172, U251 (glioblastoma); and SKMEL28, A375(M), 1011 (melanoma). Growth rates are determined by cell counting. Briefly, 5 X104 cells are plated in each well of a 24-well plate, allowed to attach overnight, and treated with compounds (e.g., Cinnamic acid: 2.5, 5, 10, 20, 30 mM) the following day. Cells are grown for 3 days at 37°C in the presence or absence of the drug, then detached with trypsin/EDTA and counted in a Coulter counter. Viability is determined by Trypan-blue exclusion assay[1].
References

[1]. Liu L, et al. Cinnamic acid: a natural product with potential use in cancer intervention. Int J Cancer. 1995 Jul 28;62(3):345-50.

 Chemical & Physical Properties

Density 1.2±0.1 g/cm3
Boiling Point 265.0±0.0 °C at 760 mmHg
Melting Point 133ºC
Molecular Formula C9H8O2
Molecular Weight 148.159
Flash Point 189.5±9.6 °C
Exact Mass 148.052429
PSA 37.30000
LogP 2.41
Vapour Pressure 0.0±0.5 mmHg at 25°C
Index of Refraction 1.616
Stability Stable. Combustible. Incompatible with strong oxidizing agents.

 MSDS

Name: Cinnamic Acid Material Safety Data Sheet
Synonym: Phenylacrylic acid; 3-Phenylacrylic acid; 3-Phenyl-2-propenoic acid
CAS: 621-82-9
Section 1 - Chemical Product MSDS Name:Cinnamic Acid Material Safety Data Sheet
Synonym:Phenylacrylic acid; 3-Phenylacrylic acid; 3-Phenyl-2-propenoic acid

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS
CAS# Chemical Name content EINECS#
621-82-9 Cinnamic Acid 100 % 210-708-3
Hazard Symbols: XI
Risk Phrases: 36/38

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation.
Ingestion:
Causes gastrointestinal irritation with nausea, vomiting and diarrhea.
Inhalation:
Causes respiratory tract irritation.
Chronic:
No information found.

Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Get medical aid if irritation develops or persists.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use foam, dry chemical, or carbon dioxide.

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Reduce airborne dust and prevent scattering by moistening with water. Clean up spills immediately, observing precautions in the Protective Equipment section.

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Wash hands before eating. Use with adequate ventilation. Avoid contact with skin and eyes. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 621-82-9: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white
Odor: Honey floral odor.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 300 deg C
Freezing/Melting Point: 133 deg C
Autoignition Temperature: Not applicable.
Flash Point: 212 deg F ( 100.00 deg C)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water: Insoluble in water.
Specific Gravity/Density: Not available.
Molecular Formula: C9H8O2
Molecular Weight: 148.0548

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidants.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 621-82-9: GD7800000 LD50/LC50:
CAS# 621-82-9: Draize test, rabbit, skin: 500 mg/24H Mild; Oral, mouse: LD50 = 5 gm/kg; Oral, rat: LD50 = 2500 mg/kg.
Carcinogenicity:
Cinnamic Acid - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

Section 12 - ECOLOGICAL INFORMATION


Section 13 - DISPOSAL CONSIDERATIONS
Products which are considered hazardous for supply are classified as Special Waste and the disposal of such chemicals is covered by regulations which may vary according to location. Contact a specialist disposal company or the local waste regulator for advice. Empty containers must be decontaminated before returning for recycling.

Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/38 Irritating to eyes and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 28 After contact with skin, wash immediately
with...
WGK (Water Danger/Protection)
CAS# 621-82-9: 1
Canada
CAS# 621-82-9 is listed on Canada's DSL List.
CAS# 621-82-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 621-82-9 is listed on the TSCA inventory.


SECTION 16 - ADDITIONAL INFORMATION
N/A

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
GD7800000
CHEMICAL NAME :
Cinnamic acid
CAS REGISTRY NUMBER :
621-82-9
LAST UPDATED :
199701
DATA ITEMS CITED :
9
MOLECULAR FORMULA :
C9-H8-O2
MOLECULAR WEIGHT :
148.17
WISWESSER LINE NOTATION :
QV1U1R

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rabbit
REFERENCE :
FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 16,687,1978 ** ACUTE TOXICITY DATA **
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 16,687,1978
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1600 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
BCFAAI Bollettino Chimico Farmaceutico. (Societa Editoriale Farmaceutica, Via Ausonio 12, 20123 Milan, Italy) V.33- 1894- Volume(issue)/page/year: 112,53,1973
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
GISAAA Gigiena i Sanitariya. For English translation, see HYSAAV. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.1- 1936- Volume(issue)/page/year: 46(1),94,1981
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
160 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 16,687,1978
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
380 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 19,617,1969
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
VPITAR Voprosy Pitaniya. Problems of Nutrition. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.1-10, 1932-41; V.11- 1952- Volume(issue)/page/year: 33(5),48,1974 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 82933 No. of Facilities: 87 (estimated) No. of Industries: 2 No. of Occupations: 10 No. of Employees: 22012 (estimated)

 Safety Information

Hazard Codes Xi
Risk Phrases R36/37/38
Safety Phrases 26-36
WGK Germany 1
RTECS GD7850000
HS Code 2916190090

 Synthetic Route

 Customs

HS Code 2916399090
Summary 2916399090 other aromatic monocarboxylic acids, their anhydrides, halides, peroxides, peroxyacids and their derivatives VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

 Synonyms

(E)-3-Phenylprop-2-enoic acid
Propenoic acid, 3-phenyl-, (trans)-
Cinnamic acid
(2E)-3-Phenylacrylic acid
trans-Cinnamic Acid
EINECS 205-398-1
MFCD00004369
QV1U1R &&Trans or E Form
2-Propenoic acid, 3-phenyl-, (2E)-
4-09-00-02002 (Beilstein Handbook Reference)
trans-b-Carboxystyrene
2-Propenoicacid, 3-phenyl-
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