Name | perillic acid |
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Synonyms |
(S)-(-)-perillyc acid
4-(1-methylethenyl)-1-cyclohexene-1-carboxylic acid (4S)-[2-propenyl]-1-cyclohexene-1-carboxylic acid 4-(prop-1-en-2-yl)cyclohex-1-ene-1-carboxylic acid MFCD02114258 4-Isopropenylcyclohex-1-enecarboxylic acid (S)-(-)-perillic cid (S)-4-(prop-1-en-2-yl)cyclohex-1-enecarboxylic acid 4-prop-1-en-2-ylcyclohexene-1-carboxylic acid (S)-(-)-4-isopropenylcyclohexene-1-carboxylic acid Perillic acid EINECS 231-709-5 4-Isopropenyl-1-cyclohexene-1-carboxylic acid |
Description | Perillic acid is the metabolite of Perillyl alcohol (HY-N7000). Perillic acid induces lung cancer cell cycle arrest and apoptosis. Perillic acid shows anti-HSV-1 and immunomodulatory activities[1][2][3]. |
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Related Catalog | |
Target |
HSV-1 |
In Vitro | Perillic acid (1-5 mM; 24 h) 以剂量依赖的方式降低 A549 细胞的存活率[1]。 Perillic acid (1 mM; 24 h) 诱导 A549 细胞 S 期阻滞,诱导 H520 细胞 G2/M 期阻滞[1]。 Perillic acid (2 mM; 24 h) 诱导 A549 和 H520 细胞凋亡[1]。 Perillic acid (0-50 μM; 24 h) 显示出主要针对 17syn+ HSV-1 的抗病毒活性 (EC50 KOS: 2.84 μM; 17syn+: 1.08 μM)[2]。 Cell Cytotoxicity Assay[1] Cell Line: A549 cells Concentration: 1, 2, 3, 4 and 5 mM Incubation Time: 24 h Result: Resulted in decreased survival in a dose-dependent manner with an IC50 of 3.6 mM. Cell Cycle Analysis[1] Cell Line: A549 and H520 cells Concentration: 1 mM Incubation Time: 24 h Result: Induced S-phase arrest in A549 cells and induced G2/M arrest in H520 cells. Apoptosis Analysis[1] Cell Line: A549 and H520 cells Concentration: 2 mM Incubation Time: 24 h Result: Increased apoptosis to 27% in A549 and to 18% in H520 cells compared to control (12%). Western Blot Analysis[1] Cell Line: H520 cells Concentration: 0.5 mM Incubation Time: 24 h Result: Increased Bax expression and decreased procaspase-3 levels. |
In Vivo | Perillic acid (50 μM/kg; i.p.; daily for 5 days) 显示小鼠免疫调节活性[3]。 Animal Model: Balb/c mice[3] Dosage: 50 μM/kg Administration: Intraperitoneal injection, daily for 5 days Result: Increased the total white blood cells (WBC) count. Increased the total antibody production, antibody producing cells in spleen, bone marrow cellularity and α-esterase positive cells significantly compared to the normal animals. |
References |
Density | 1.068 g/cm3 |
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Boiling Point | 284.9ºC at 760 mmHg |
Melting Point | 129-131 °C(lit.) |
Molecular Formula | C10H14O2 |
Molecular Weight | 166.21700 |
Flash Point | 134ºC |
Exact Mass | 166.09900 |
PSA | 37.30000 |
LogP | 2.37360 |
Index of Refraction | 1.513 |
Storage condition | 2-8°C |
Synonym:None Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS
Risk Phrases: 36/37/38 Section 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.The toxicological properties of this material have not been fully investigated. Potential Health Effects Eye: Causes eye irritation. The toxicological properties of this material have not been fully investigated. Skin: Causes skin irritation. The toxicological properties of this material have not been fully investigated. Ingestion: Causes gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated. Inhalation: Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. 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. Skin: Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse. Ingestion: Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. 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. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Extinguishing Media: In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam. Section 6 - ACCIDENTAL RELEASE MEASURES General Information: Use proper personal protective equipment as indicated in Section 8. Spills/Leaks: Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal. Avoid generating dusty conditions. Provide ventilation. Section 7 - HANDLING and STORAGE Handling: Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Storage: Store in a cool, dry place. Keep container closed when not in use. Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION Engineering Controls: Use adequate general or local exhaust ventilation to keep airborne concentrations below the permissible exposure limits. Use process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels. Exposure Limits CAS# 7694-45-3: 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 gloves to prevent skin exposure. Clothing: Wear appropriate protective clothing to minimize contact with skin. Respirators: Wear a NIOSH/MSHA or European Standard EN 149 approved full-facepiece airline respirator in the positive pressure mode with emergency escape provisions. Section 9 - PHYSICAL AND CHEMICAL PROPERTIES Physical State: Solid Color: cream Odor: None reported. pH: Not available. Vapor Pressure: Not available. Viscosity: Not available. Boiling Point: Not available. Freezing/Melting Point: 129.00 - 131.00 deg C Autoignition Temperature: Not available. Flash Point: Not available. Explosion Limits, lower: N/A Explosion Limits, upper: N/A Decomposition Temperature: Solubility in water: Specific Gravity/Density: Molecular Formula: C10H14O2 Molecular Weight: 166.22 Section 10 - STABILITY AND REACTIVITY Chemical Stability: Stable under normal temperatures and pressures. Conditions to Avoid: Incompatible materials, strong oxidants. Incompatibilities with Other Materials: Oxidizing agents. Hazardous Decomposition Products: Irritating and toxic fumes and gases. Hazardous Polymerization: Has not been reported. Section 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 7694-45-3: GW4564565 LD50/LC50: Not available. Carcinogenicity: L-(-)-Perillic 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 Dispose of in a manner consistent with federal, state, and local regulations. 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 36/37/38 Irritating to eyes, respiratory system and skin. Safety Phrases: S 24/25 Avoid contact with skin and eyes. WGK (Water Danger/Protection) CAS# 7694-45-3: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 7694-45-3 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 7694-45-3 is not listed on the TSCA inventory. It is for research and development use only. SECTION 16 - ADDITIONAL INFORMATION N/A |
Hazard Codes | Xi: Irritant; |
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Risk Phrases | 36/37/38 |
Safety Phrases | S26-S36 |
WGK Germany | 3 |
HS Code | 2916209090 |
Precursor 0 | |
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DownStream 1 | |
HS Code | 2916209090 |
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Summary | 2916209090 other cyclanic, cyclenic or cyclotherpenic monocarboxylic acids, their anhydrides, halides, peroxides, peroxyacids and their derivatives VAT:17.0% Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) MFN tariff:6.5% General tariff:30.0% |