(S)-(-)-PERILLIC ACID

Modify Date: 2024-01-05 00:41:00

(S)-(-)-PERILLIC ACID Structure
(S)-(-)-PERILLIC ACID structure
Common Name (S)-(-)-PERILLIC ACID
CAS Number 7694-45-3 Molecular Weight 166.21700
Density 1.068 g/cm3 Boiling Point 284.9ºC at 760 mmHg
Molecular Formula C10H14O2 Melting Point 129-131 °C(lit.)
MSDS N/A Flash Point 134ºC

 Use of (S)-(-)-PERILLIC ACID


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].

 Names

Name perillic acid
Synonym More Synonyms

 (S)-(-)-PERILLIC ACID Biological Activity

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].
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

[1]. Yeruva L, et al. Perillyl alcohol and perillic acid induced cell cycle arrest and apoptosis in non small cell lung cancer cells. Cancer Lett. 2007 Nov 18;257(2):216-26.  

[2]. Mello CP, et al. Perillyl alcohol and perillic acid exert efficient action upon HSV-1 maturation and release of infective virus. Antivir Ther. 2020;25(1):1-11.  

[3]. Raphael TJ, et al. Immunomodulatory activity of naturally occurring monoterpenes carvone, limonene, and perillic acid. Immunopharmacol Immunotoxicol. 2003 May;25(2):285-94.  

 Chemical & Physical Properties

Density 1.068 g/cm3
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

 MSDS

Name: L-(-)-Perillic Acid 95% Material Safety Data Sheet
Synonym: None
CAS: 7694-45-3
Section 1 - Chemical Product MSDS Name:L-(-)-Perillic Acid 95% Material Safety Data Sheet
Synonym:None

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS
CAS# Chemical Name content EINECS#
7694-45-3 L-(-)-Perillic Acid 95 231-709-5
Hazard Symbols: XI
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

 Safety Information

Hazard Codes Xi: Irritant;
Risk Phrases 36/37/38
Safety Phrases S26-S36
WGK Germany 3
HS Code 2916209090

 Precursor & DownStream

Precursor  0

DownStream  1

 Customs

HS Code 2916209090
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%

 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