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(S)-(-)-LIMONENE

CAS No.: 5989-54-8
Formula: C10H16
Molecular Weight: 136.23
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What is (S)-(-)-LIMONENE

(4S)-Limonene is a naturally occurring monoterpene found in the essential oils of citrus fruits, particularly in the peels of oranges, lemons, and limes. Known for its fresh, citrusy aroma, it is widely used in the food, fragrance, and cleaning industries as a flavoring agent, fragrance additive, and natural solvent. (4S)-Limonene is the S-enantiomer of limonene, distinguished by its specific molecular configuration, which contributes to its unique properties. Beyond its industrial applications, it has gained attention for its potential health benefits, including antioxidant, anti-inflammatory, and anticancer properties. As a sustainable and renewable resource, (4S)-limonene is a versatile compound with growing importance in green chemistry and eco-friendly product development.

Preparation Process: (4S)-Limonene can be prepared through the fractional distillation of citrus peel oils, primarily from oranges, which naturally contain high concentrations of (4S)-limonene. The process involves steam distillation of citrus peels to extract the essential oil, followed by fractional distillation under reduced pressure to isolate (4S)-limonene with high purity. Alternatively, enantioselective synthesis can be achieved via asymmetric hydrogenation of myrcene using a chiral catalyst, such as a rhodium complex with (R)-BINAP, to favor the (4S)-enantiomer. Another method involves the enzymatic resolution of racemic limonene using lipases to selectively hydrolyze the (4R)-enantiomer, leaving (4S)-limonene enriched. Purification is typically performed via column chromatography.

Usage Scenarios: (4S)-Limonene, a monoterpene found in citrus peels, is widely used in the food, fragrance, and pharmaceutical industries. As a flavoring agent, it imparts a citrusy aroma to foods and beverages. In perfumery, it serves as a natural solvent and fragrance enhancer. Industrially, it acts as a biodegradable cleaning agent and degreaser. In pharmaceuticals, (4S)-limonene exhibits potential therapeutic effects, including anti-inflammatory, antioxidant, and anticancer properties. It is also studied for its role in drug delivery systems due to its lipophilic nature. Additionally, it serves as a precursor in the synthesis of other valuable compounds, such as carvone and menthol.

(S)-(-)-LIMONENE Basic Info
Chemical Name (S)-(-)-LIMONENE
Synonyms L-LIMONENE;(-)-Limonene;(S)-1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-ene;beta-limonene;(s)-(-)-p-mentha-8-diene;(-)-1,8-p-menthadiene,(S)-(-)-limonene;(S)-(-)-4-ISOPROPENYL-1-METHYL-1-CYCLOHEXENE;1-methyl-4-(1-methylethenyl)-,(S)-Cyclohexene;cyclohexene,1-methyl-4-(1-methylethenyl)-,(S)-;LIMONENER
CAS No. 5989-54-8
Molecular Formula C10H16
Molecular Weight 136.23
PSA 0.00000
LogP 4.38 at 37℃
Safely Info
RTECS OS8350000
Hazard Class 3
Safety Statements 24-37-60-61
HS Code 29029090
WGK Germany -
Packing Group III
RIDADR UN 2052 3/PG 3
Risk Statements 10-38-43-50/53
Hazard Codes Xi,N
Caution Statement P210-P273-P280-P301+P310+P331-P302+P352
Hazard Declaration H226-H304-H317-H400
Symbol GHS02,GHS07,GHS08,GHS09
Signal Word Danger
(S)-(-)-LIMONENE Price
United States: $10-20
China: $5-15
Russia: $8-18
Germany: $15-25
India: $3-8
Japan: $20-30
Brazil: $7-17
South Korea: $12-22
Philippines: $5-10
United Kingdom: $15-25
France: $18-28
Mexico: $6-16
Canada: $10-20
South Africa: $9-19
Egypt: $6-12
Turkey: $7-17
Thailand: $5-10
Indonesia: $4-9
MSDS
MSDS
Name: (-)-Limonene 92% Material Safety Data Sheet
Synonym: (S)-Limonene; l-Limonene
CAS: 5989-54-8
Section 1 - Chemical Product   MSDS Name:(-)-Limonene 92% Material Safety Data Sheet
Synonym:(S)-Limonene; l-Limonene

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS
CAS# Chemical Name content EINECS#
5989-54-8 (-)-Limonene 92 227-815-6
Hazard Symbols: XI N
Risk Phrases: 10 38 43 50/53

Section 3 - HAZARDS IDENTIFICATION
  EMERGENCY OVERVIEW
Flammable. Irritating to skin. May cause sensitization by skin contact. Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May cause an allergic reaction in certain individuals.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Vapors may cause dizziness or suffocation.
Chronic:
No information found.

Section 4 - FIRST AID MEASURES
  Eyes: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid.
Skin:
In case of contact, immediately flush skin with soap and plenty of water. Remove contaminated clothing and shoes. Get medical aid if symptoms occur. Wash clothing before reuse.
Ingestion:
If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
If inhaled, remove to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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. Vapors may form an explosive mixture with air.
During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Use water spray to keep fire-exposed containers cool. Containers may explode in the heat of a fire. Flammable liquid and vapor. Vapors are heavier than air and may travel to a source of ignition and flash back. Vapors can spread along the ground and collect in low or confined areas.
Extinguishing Media:
For small fires, use dry chemical, carbon dioxide, water spray or alcohol-resistant foam. For large fires, use water spray, fog, or alcohol-resistant foam. Use water spray to cool fire-exposed containers. Water may be ineffective. Do NOT use straight streams of water.

Section 6 - ACCIDENTAL RELEASE MEASURES
  General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Clean up spills immediately, observing precautions in the Protective Equipment section. Remove all sources of ignition. Use a spark-proof tool. Provide ventilation. A vapor suppressing foam may be used to reduce vapors.

Section 7 - HANDLING and STORAGE
  Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Ground and bond containers when transferring material. Use spark-proof tools and explosion proof equipment. Avoid contact with eyes, skin, and clothing. Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Keep container tightly closed. Keep away from heat, sparks and flame. Avoid ingestion and inhalation. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames.
Storage:
Keep away from heat, sparks, and flame. Keep away from sources of ignition. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
Flammables-area.

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
  Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 5989-54-8: 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: Liquid
Color: clear, colorless
Odor: citrus-like odor
pH: Not available.
Vapor Pressure: 1.44 mm Hg @ 25 deg C
Viscosity: Not available.
Boiling Point: 175-177 deg C @ 760 mmHg
Freezing/Melting Point: -74 deg C
Autoignition Temperature: 255 deg C ( 491.00 deg F)
Flash Point: 48 deg C ( 118.40 deg F)
Explosion Limits, lower: .70 vol %
Explosion Limits, upper: 6.10 vol %
Decomposition Temperature:
Solubility in water: practically insoluble
Specific Gravity/Density: .8420 g/cm3
Molecular Formula: C10H16
Molecular Weight: 136.24

Section 10 - STABILITY AND REACTIVITY
  Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Ignition sources, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported.

Section 11 - TOXICOLOGICAL INFORMATION
  RTECS#:
CAS# 5989-54-8: OS8350000 LD50/LC50:
CAS# 5989-54-8: Draize test, rabbit, skin: 500 mg/24H Moderate.
Carcinogenicity:
(-)-Limonene - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

Section 12 - ECOLOGICAL INFORMATION
  Other No information available.

Section 13 - DISPOSAL CONSIDERATIONS
  Dispose of in a manner consistent with federal, state, and local regulations.

Section 14 - TRANSPORT INFORMATION
 
IATA
Shipping Name: Dipentene
Hazard Class: 3
UN Number: 2052
Packing Group: III
IMO
Shipping Name: Dipentene
Hazard Class: 3.3
UN Number: 2052
Packing Group: III
RID/ADR
Shipping Name: Dipentene
Hazard Class: 3
UN Number: 2052
Packing group: III

Section 15 - REGULATORY INFORMATION
 
European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI N
Risk Phrases:
R 10 Flammable.
R 38 Irritating to skin.
R 43 May cause sensitization by skin contact.
R 50/53 Very toxic to aquatic organisms, may cause
long-term adverse effects in the aquatic environment.
Safety Phrases:
S 24 Avoid contact with skin.
S 37 Wear suitable gloves.
S 60 This material and its container must be
disposed of as hazardous waste.
S 61 Avoid release to the environment. Refer to
special instructions/safety data sheets.
WGK (Water Danger/Protection)
CAS# 5989-54-8: 1
Canada
CAS# 5989-54-8 is listed on Canada's DSL List.
CAS# 5989-54-8 is listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 5989-54-8 is listed on the TSCA inventory.


SECTION 16 - ADDITIONAL INFORMATION
N/A
SDS 1.0
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