(-)-(1R,3R,4S)-Menthol (CAS 98167-53-4) — formula C10H20O, molecular weight 156.26.
(-)-(1R,3R,4S)-Menthol (CAS 98167-53-4) is classified under Food Additives, with molecular formula C10H20O and molecular weight 156.26, and serves as a key raw material in the food and beverage industry — commonly applied as a food additive, nutritional supplement, or processing aid where regulatory-grade purity is required. Jinan Shenghe Chemical Co., Ltd. supplies (-)-(1R,3R,4S)-Menthol at commercial scale with stable lot-to-lot quality, accompanied by COA and full specification documentation. Typical categorization: Food Additives.
| CAS Number | 98167-53-4 |
|---|---|
| Molecular Formula | C10H20O |
| Molecular Weight | 156.26 |
| Melting Point | 100 °F (NTP, 1992) |
| Boiling Point | 421 °F at 760 mmHg (NTP, 1992) |
| LogP | 3 |
| Applications | Uses: Found in peppermint oil and other mint oils, [Merck Index] Used as flavoring, fragrance agent in toothpastes, mouthwashes, pharmaceuticals, cigarettes, aerosol room fresheners, cosmetics, liqueurs, confectionary, and perfumes, Also used as a topical antipruritic and in cough drops and inhalers, [HSDB] Used in Canada to control mites and in Europe in paints and lacquers, adhesives, metal care products, cleaning products, shoe and leather polishes, disinfectants, solvents, repellents, and animal care products, [eChemPortal: SIDSUNEP] Peppermint oil contains menthol, menthone, and more than 30 other chemicals. It is widely used as a flavoring agent and herbal remedy. [Haddad, p. 1439], Painting (Solvents) [Category: Paint], Working with Glues and Adhesives [Category: Other], Using Disinfectants or Biocides [Category: Clean], For menthol (USEPA, OPP Pesticide Code: 051601) ACTIVE products with label matches., SRP: Registered for use in the USA but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses., Flavor in liquers, perfumery, cough drops, and nasal inhalers., L-Menthol, Because of its cooling and refreshing effect, (-)-menthol is used in large quantities in cigarettes, toothpastes, chewing gum, sweets, and medicines., Menthol, which provides a cooling sensation, is a common constituent of after-shaves., For more Uses (Complete) data for MENTHOL (10 total), please visit the HSDB record page., Menthol has local anesthetic and counterirritant qualities, and it is widely used to relieve minor throat irritation. Menthol is also used to prepare menthyl esters to emphasize floral notes (especially rose) (L1263). Used to treat occasional minor irritation, pain, sore mouth, and sore throat as well as cough associated with a cold or inhaled irritants., Use Classification: Fragrance Ingredients, Fragrance Ingredients, Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes, Flavoring Agents -> JECFA Flavorings Index, Cosmetics -> Soothing, Denaturant, Masking, Refreshing, Industry Uses: Odor agents, Odor agents, Fragrance, Consumer Uses: Fragrance, Household Products: Cosmetics product ingredient: Menthol (dl-menthol, l-menthol, d-menthol), Menthol is a fragrance allergen. Fragrance allergens are hazardous only to individuals who suffer from fragrance allergies. The Cosmetic Fragrance and Flavor Ingredient Right to Know Act of 2020 requires fragrance allergens included in Annex III of the EU Cosmetics Regulation No. 1223, 2009 be reported to the California Department of Public Health. Fragrance allergens are only required to be reported if present in a rinse-off cosmetic product at a concentration at or above 0.01 percent (100 parts per million) or in a leave-on cosmetic product at a concentration at or above 0.001 percent (10 parts per million)., For more information, you can visit the fragrance allergens webpage on the California Safe Cosmetics Program website:, https:, www.cdph.ca.gov, Programs, CCDPHP, DEODC, OHB, CSCP, Pages, FragranceAllergens.aspx, Product count: 1285, Information on 149 consumer products that contain Menthol in the following categories is provided:, • Commercial, Institutional, • Inside the Home, • Personal Care, • Pet Care, Information on 35 consumer products that contain Menthol (Racementhol) in the following categories is provided:, Methods of Manufacturing: (-)-Menthol from (+-)-Menthol. (+-)-Menthol can be prepared via several routes and subsequently resolved into the optical isomers: a. Racemic menthol can be synthesized by hydrogenation of thymol. This yields a mixture containing the four stereoisomeric menthols in various proportions. (+-)-Menthol is separated from the other isomers by distillation. The remaining isomeric menthols, neomenthol, isomenthol, and a trace of neoisomenthol, can be epimerized, under the conditions used for the thymol hydrogenation, to give ca. 6:3:1 equilibrium mixture of (+-)-menthol, (+-)-neomenthol, and (+-)-isomenthol, respectively. (+-)-Menthol can, again, be distilled from the equilibrium mixture. b. (+-)-Menthol can be resolved into its optical antipodes by several routes. A large-scale industrial process utilizes selective crystallization of either (+)- or (-)-menthyl benzoate by seeding saturated solutions or supercooled melts of (+-)-menthyl benzoates with crystals of (+)- or (-)-menthyl benzoate. Pure (+)- or (-)-menthol is obtained following hydrolysis of the esters. The undesired (+)-menthol can be reconverted into the racemate. Biochemical resolution methods have also been developed., (-)-Menthol can also be prepared from (-)-piperitone, the main component of Eucalyptus dives Typus oils. Hydrogenation in the presence of Raney nickel yields a mixture of menthols, from which (-)-menthol can be separated by crystallization and saponification of its chloroacetate., (-)-Menthol from (+)-Citronellal. This process uses the readily occurring cyclization of citronellal to isopulegol. (+)-Citronellal can be isolated with an optical purity of about 80% from citronella oil. Alternatively, it can be synthesized with a purity of 98% from dialkylgeranylamine (obtained from myrcene and a dialkylamine) by enantioselective isomerization to (+)-citronellaldialkylenamine followed by hydrolytic cleavage to (+)-citronellal. Isomerization is effected in the presence of a chiral rhodium-phosphine complex as a catalyst. (+)-Citronellal is cyclized in the presence of acidic catalysts (e.g., silica gel) to give a mixture of optically active isopulegol isomers containing about 20% of the corresponding racemates. (-)-Isopulegol can be isolated from this mixture and hydrogenated to (-)-menthol. The remaining isopulegol stereoisomers can be partly reconverted into (+)-citronellal by pyrolytic cleavage and reused in the cyclization procedure. |
Documented applications: Uses: Found in peppermint oil and other mint oils, [Merck Index] Used as flavoring, fragrance agent in toothpastes, mouthwashes, pharmaceuticals, cigarettes, aerosol room fresheners, cosmetics, liqueurs, confectionary, and perfumes, Also used as a topical antipruritic and in cough drops and inhalers, [HSDB] Used in Canada to control mites and in Europe in paints and lacquers, adhesives, metal care products, cleaning products, shoe and leather polishes, disinfectants, solvents, repellents, and animal care products, [eChemPortal: SIDSUNEP] Peppermint oil contains menthol, menthone, and more than 30 other chemicals. It is widely used as a flavoring agent and herbal remedy. [Haddad, p. 1439], Painting (Solvents) [Category: Paint], Working with Glues and Adhesives [Category: Other], Using Disinfectants or Biocides [Category: Clean], For menthol (USEPA, OPP Pesticide Code: 051601) ACTIVE products with label matches., SRP: Registered for use in the USA but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses., Flavor in liquers, perfumery, cough drops, and nasal inhalers., L-Menthol, Because of its cooling and refreshing effect, (-)-menthol is used in large quantities in cigarettes, toothpastes, chewing gum, sweets, and medicines., Menthol, which provides a cooling sensation, is a common constituent of after-shaves., For more Uses (Complete) data for MENTHOL (10 total), please visit the HSDB record page., Menthol has local anesthetic and counterirritant qualities, and it is widely used to relieve minor throat irritation. Menthol is also used to prepare menthyl esters to emphasize floral notes (especially rose) (L1263). Used to treat occasional minor irritation, pain, sore mouth, and sore throat as well as cough associated with a cold or inhaled irritants., Use Classification: Fragrance Ingredients, Fragrance Ingredients, Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes, Flavoring Agents -> JECFA Flavorings Index, Cosmetics -> Soothing, Denaturant, Masking, Refreshing, Industry Uses: Odor agents, Odor agents, Fragrance, Consumer Uses: Fragrance, Household Products: Cosmetics product ingredient: Menthol (dl-menthol, l-menthol, d-menthol), Menthol is a fragrance allergen. Fragrance allergens are hazardous only to individuals who suffer from fragrance allergies. The Cosmetic Fragrance and Flavor Ingredient Right to Know Act of 2020 requires fragrance allergens included in Annex III of the EU Cosmetics Regulation No. 1223, 2009 be reported to the California Department of Public Health. Fragrance allergens are only required to be reported if present in a rinse-off cosmetic product at a concentration at or above 0.01 percent (100 parts per million) or in a leave-on cosmetic product at a concentration at or above 0.001 percent (10 parts per million)., For more information, you can visit the fragrance allergens webpage on the California Safe Cosmetics Program website:, https:, www.cdph.ca.gov, Programs, CCDPHP, DEODC, OHB, CSCP, Pages, FragranceAllergens.aspx, Product count: 1285, Information on 149 consumer products that contain Menthol in the following categories is provided:, • Commercial, Institutional, • Inside the Home, • Personal Care, • Pet Care, Information on 35 consumer products that contain Menthol (Racementhol) in the following categories is provided:, Methods of Manufacturing: (-)-Menthol from (+-)-Menthol. (+-)-Menthol can be prepared via several routes and subsequently resolved into the optical isomers: a. Racemic menthol can be synthesized by hydrogenation of thymol. This yields a mixture containing the four stereoisomeric menthols in various proportions. (+-)-Menthol is separated from the other isomers by distillation. The remaining isomeric menthols, neomenthol, isomenthol, and a trace of neoisomenthol, can be epimerized, under the conditions used for the thymol hydrogenation, to give ca. 6:3:1 equilibrium mixture of (+-)-menthol, (+-)-neomenthol, and (+-)-isomenthol, respectively. (+-)-Menthol can, again, be distilled from the equilibrium mixture. b. (+-)-Menthol can be resolved into its optical antipodes by several routes. A large-scale industrial process utilizes selective crystallization of either (+)- or (-)-menthyl benzoate by seeding saturated solutions or supercooled melts of (+-)-menthyl benzoates with crystals of (+)- or (-)-menthyl benzoate. Pure (+)- or (-)-menthol is obtained following hydrolysis of the esters. The undesired (+)-menthol can be reconverted into the racemate. Biochemical resolution methods have also been developed., (-)-Menthol can also be prepared from (-)-piperitone, the main component of Eucalyptus dives Typus oils. Hydrogenation in the presence of Raney nickel yields a mixture of menthols, from which (-)-menthol can be separated by crystallization and saponification of its chloroacetate., (-)-Menthol from (+)-Citronellal. This process uses the readily occurring cyclization of citronellal to isopulegol. (+)-Citronellal can be isolated with an optical purity of about 80% from citronella oil. Alternatively, it can be synthesized with a purity of 98% from dialkylgeranylamine (obtained from myrcene and a dialkylamine) by enantioselective isomerization to (+)-citronellaldialkylenamine followed by hydrolytic cleavage to (+)-citronellal. Isomerization is effected in the presence of a chiral rhodium-phosphine complex as a catalyst. (+)-Citronellal is cyclized in the presence of acidic catalysts (e.g., silica gel) to give a mixture of optically active isopulegol isomers containing about 20% of the corresponding racemates. (-)-Isopulegol can be isolated from this mixture and hydrogenated to (-)-menthol. The remaining isopulegol stereoisomers can be partly reconverted into (+)-citronellal by pyrolytic cleavage and reused in the cyclization procedure..
(-)-(1R,3R,4S)-Menthol is a chemical compound with CAS registry number 98167-53-4 and molecular formula C10H20O (molecular weight 156.26).
CAS number: 98167-53-4
Its molecular formula C10H20O comprises 10 C, 20 H, 1 O atoms.
Also known as: (-)-(1R,3R,4S)-Menthol · (-)-(1R,3R,4S)-薄荷醇
The CAS registry number of (-)-(1R,3R,4S)-Menthol is 98167-53-4.
Molecular formula C10H20O, molecular weight 156.26.
It is also registered under: (-)-(1R,3R,4S)-Menthol, (-)-(1R,3R,4S)-薄荷醇.
Recorded applications: Uses: Found in peppermint oil and other mint oils, [Merck Index] Used as flavoring, fragrance agent in toothpastes, mouthwashes, pharmaceuticals, cigarettes, aerosol room fresheners, cosmetics, liqueurs, confectionary, and perfumes, Also used as a topical antipruritic and in cough drops and inhalers, [HSDB] Used in Canada to control mites and in Europe in paints and lacquers, adhesives, metal care products, cleaning products, shoe and leather polishes, disinfectants, solvents, repellents, and animal care products, [eChemPortal: SIDSUNEP] Peppermint oil contains menthol, menthone, and more than 30 other chemicals. It is widely used as a flavoring agent and herbal remedy. [Haddad, p. 1439], Painting (Solvents) [Category: Paint], Working with Glues and Adhesives [Category: Other], Using Disinfectants or Biocides [Category: Clean], For menthol (USEPA, OPP Pesticide Code: 051601) ACTIVE products with label matches., SRP: Registered for use in the USA but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses., Flavor in liquers, perfumery, cough drops, and nasal inhalers., L-Menthol, Because of its cooling and refreshing effect, (-)-menthol is used in large quantities in cigarettes, toothpastes, chewing gum, sweets, and medicines., Menthol, which provides a cooling sensation, is a common constituent of after-shaves., For more Uses (Complete) data for MENTHOL (10 total), please visit the HSDB record page., Menthol has local anesthetic and counterirritant qualities, and it is widely used to relieve minor throat irritation. Menthol is also used to prepare menthyl esters to emphasize floral notes (especially rose) (L1263). Used to treat occasional minor irritation, pain, sore mouth, and sore throat as well as cough associated with a cold or inhaled irritants., Use Classification: Fragrance Ingredients, Fragrance Ingredients, Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes, Flavoring Agents -> JECFA Flavorings Index, Cosmetics -> Soothing, Denaturant, Masking, Refreshing, Industry Uses: Odor agents, Odor agents, Fragrance, Consumer Uses: Fragrance, Household Products: Cosmetics product ingredient: Menthol (dl-menthol, l-menthol, d-menthol), Menthol is a fragrance allergen. Fragrance allergens are hazardous only to individuals who suffer from fragrance allergies. The Cosmetic Fragrance and Flavor Ingredient Right to Know Act of 2020 requires fragrance allergens included in Annex III of the EU Cosmetics Regulation No. 1223, 2009 be reported to the California Department of Public Health. Fragrance allergens are only required to be reported if present in a rinse-off cosmetic product at a concentration at or above 0.01 percent (100 parts per million) or in a leave-on cosmetic product at a concentration at or above 0.001 percent (10 parts per million)., For more information, you can visit the fragrance allergens webpage on the California Safe Cosmetics Program website:, https:, www.cdph.ca.gov, Programs, CCDPHP, DEODC, OHB, CSCP, Pages, FragranceAllergens.aspx, Product count: 1285, Information on 149 consumer products that contain Menthol in the following categories is provided:, • Commercial, Institutional, • Inside the Home, • Personal Care, • Pet Care, Information on 35 consumer products that contain Menthol (Racementhol) in the following categories is provided:, Methods of Manufacturing: (-)-Menthol from (+-)-Menthol. (+-)-Menthol can be prepared via several routes and subsequently resolved into the optical isomers: a. Racemic menthol can be synthesized by hydrogenation of thymol. This yields a mixture containing the four stereoisomeric menthols in various proportions. (+-)-Menthol is separated from the other isomers by distillation. The remaining isomeric menthols, neomenthol, isomenthol, and a trace of neoisomenthol, can be epimerized, under the conditions used for the thymol hydrogenation, to give ca. 6:3:1 equilibrium mixture of (+-)-menthol, (+-)-neomenthol, and (+-)-isomenthol, respectively. (+-)-Menthol can, again, be distilled from the equilibrium mixture. b. (+-)-Menthol can be resolved into its optical antipodes by several routes. A large-scale industrial process utilizes selective crystallization of either (+)- or (-)-menthyl benzoate by seeding saturated solutions or supercooled melts of (+-)-menthyl benzoates with crystals of (+)- or (-)-menthyl benzoate. Pure (+)- or (-)-menthol is obtained following hydrolysis of the esters. The undesired (+)-menthol can be reconverted into the racemate. Biochemical resolution methods have also been developed., (-)-Menthol can also be prepared from (-)-piperitone, the main component of Eucalyptus dives Typus oils. Hydrogenation in the presence of Raney nickel yields a mixture of menthols, from which (-)-menthol can be separated by crystallization and saponification of its chloroacetate., (-)-Menthol from (+)-Citronellal. This process uses the readily occurring cyclization of citronellal to isopulegol. (+)-Citronellal can be isolated with an optical purity of about 80% from citronella oil. Alternatively, it can be synthesized with a purity of 98% from dialkylgeranylamine (obtained from myrcene and a dialkylamine) by enantioselective isomerization to (+)-citronellaldialkylenamine followed by hydrolytic cleavage to (+)-citronellal. Isomerization is effected in the presence of a chiral rhodium-phosphine complex as a catalyst. (+)-Citronellal is cyclized in the presence of acidic catalysts (e.g., silica gel) to give a mixture of optically active isopulegol isomers containing about 20% of the corresponding racemates. (-)-Isopulegol can be isolated from this mixture and hydrogenated to (-)-menthol. The remaining isopulegol stereoisomers can be partly reconverted into (+)-citronellal by pyrolytic cleavage and reused in the cyclization procedure..
Independent reference data for (-)-(1R,3R,4S)-Menthol (CAS 98167-53-4), compiled from public chemistry databases.
| CAS 号 | 98167-53-4 |
|---|---|
| PubChem CID | 1254 |
| 分子式 | C10H20O |
| IUPAC 名称 | 5-methyl-2-propan-2-ylcyclohexan-1-ol |
| UNII（FDA） | L7T10EIP3A |
| FEMA 编号 | 2665 |
| JECFA 编号 | 427 |
| Molecular Weight | 156.26 |
|---|---|
| XLogP3 | 3 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 1 |
| Exact Mass | 156.151415257 |
| Monoisotopic Mass | 156.151415257 |
| Topological Polar Surface Area | 20.2 |
| Heavy Atom Count | 11 |
| Boiling Point | 421 °F at 760 mmHg (NTP, 1992) |
|---|---|
| Boiling Point | 214.6 °C |
| Boiling Point | 214.00 to 216.00 °C. @ 760.00 mm Hg |
| Boiling Point | 212 °C ((-)-isomer 216.5) |
| Melting Point | 100 °F (NTP, 1992) |
| Melting Point | -8 °C |
| Flash Point | 196 °F (NTP, 1992) |
| Solubility | In water, 420 mg/L at 25 °C |
| Solubility | In water, 456 mg/L at 25 °C |
| Solubility | 0.42 mg/mL at 25 °C |
MENTHOL; 1490-04-6; 2-Isopropyl-5-methylcyclohexanol; Menthyl alcohol; Mentholum; Caswell No. 540; Mineral ice; 5-Methyl-2-(1-methylethyl)cyclohexanol; 3-Hydroxy-p-menthane; 2-Isopropyl-5-methylcyclohexan-1-ol; CCRIS 9231; DTXSID8029650; EINECS 216-074-4; EPA Pesticide Chemical Code 051601; HSDB 593; AI3-08161
| 法规与食品接触 | EU Flavoring substances FDA Substance added to food: FLAVORING AGENT OR ADJUVANT Flavoring Agents FLAVOURING_AGENT: Flavouring Agent Mint, Cool JECFA ADI: 0-4 mg/kg bw |
|---|---|
| GHS 通报统计 | 0.4% (7 / 1989) |
| GHS 通报统计 | 0.4% (7 / 1989) |
|---|---|
| 已通报的危害声明 | H315 (97.3%), H319 (82.9%), H318, H335, H402, H412 |
(-)-(1R,3R,4S)-薄荷醇 · CAS 98167-53-4 · C10H20O. UNII L7T10EIP3A. Boiling Point: 421 °F at 760 mmHg (NTP, 1992); Boiling Point: 214.6 °C; Boiling Point: 214.00 to 216.00 °C. @ 760.00 mm Hg.
Source: PubChem / Wikidata; the batch COA governs where values differ.
Supplier: Jinan Shenghe Chemical Co., Ltd.
中文页面: (-)-(1R,3R,4S)-薄荷醇