4-Methoxybenzyl alcohol
(4-METHOXYPHENYL)METHANOL · ANISYL ALCOHOL · PMBOH · ANISE ALCOHOL · ANISIC ALCOHOL · FEMA 2099 · P-ANISYL ALCOHOL · P-ANISIC ALCOHOL
Identifiers & Physical Properties
| CAS No. | 105-13-5 |
|---|---|
| Molecular formula | C8H10O2 |
| Average molar mass | 138.16 g/mol |
| Monoisotopic mass | 138.06807956 g/mol |
| SMILES | COc1ccc(CO)cc1 |
| InChIKey | MSHFRERJPWKJFX-UHFFFAOYSA-N |
| PubChem CID | 7738 |
| ChEMBL | CHEMBL294431 |
| ChEBI | CHEBI:193647 |
| EC No. | 203-273-6 |
| DTXSID | DTXSID6044357 |
Chemical & Physical Properties
| XLogP | 1.1 |
|---|---|
| Topological polar surface area | 29.5 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 2 |
| Heavy atoms | 10 |
| Formal charge | 0 |
| Complexity | 85 |
| LogP (partition coefficient) | 1.10 |
| Density | 1.107-1.1151.108 @25 °C1.113 g/mL at 25 °C (lit.) |
| Solubility | 2 mg/mL at 20 °Cinsoluble in waterpoorly soluble in glycols, glycerolsoluble in organic solvents, oilsmiscible above 20� (in ethanol)alcohol: freely soluble |
| Boiling point | 259.00 to 260.00 °C. @ 760.00 mm Hg259 °C259.1 °C @760 [mm Hg]259 °C (lit.) |
| Melting point | 24 - 25 °C22-25 °C (lit.) |
| Vapor pressure | 0.0038 [mmHg]0.24-0.53Pa at 25℃ |
| Refractive index | 1.540-1.547n20/D 1.544(lit.) |
| Physical Description | Liquidmp = 24-25 deg C[Merck Index] White liquid or low-melting solidmp = 22-25 deg C[Alfa Aesar MSDS]colourless to slightly yellow liquid or opaque crystalline mass with a mild, sweet, floral odour |
| Kovats Retention Index | 1246.812701242124412671249127312791278129512771282130313041307130813121284129012752290226823052302 |
| FEMA | 2099 | ANISYL ALCOHOL |
| FLAVIS Number | 02.128 | p-Anisyl alcohol |
| Flash point | 230 °F |
| Storage conditions | -20°C |
| Physical state | Liquid After Melting |
| pKa (acidity coefficient) | 14.43±0.10(Predicted) |
| Specific gravity | 1.108 |
| Color | Clear colorless to yellow |
| pH | 6.3 (10g/l, H2O, 20℃) |
| Odor | at 100.00 %. sweet powdery hawthorn lilac rose floral hyacinth |
| Odor type | powdery |
| Biological source | synthetic |
| Viscosity | 19.02mm2/s |
| Explosive limits | 0.9-7.3%(V) |
| Merck | 14,665 |
| JECFA Number | 871 |
| BRN | 636654 |
| Major applications | cleaning productscosmeticsenvironmentalflavors and fragrancesfood and beveragespersonal care |
| Cosmetics Ingredients Functions | PERFUMING |
| InChI | 1S/C8H10O2/c1-10-8-4-2-7(6-9)3-5-8/h2-5,9H,6H2,1H3 |
| InChIKey | MSHFRERJPWKJFX-UHFFFAOYSA-N |
| SMILES | COc1ccc(CO)cc1 |
| LogP (partition coefficient) | -0.08-1.05 at 24-27℃ |
| CAS DataBase Reference | 105-13-5(CAS DataBase Reference) |
| Substances Added to Food (formerly EAFUS) | ANISYL ALCOHOL |
| EWG's Food Scores | 2-5 |
| FDA UNII | 7N6XGV3U49 |
| NIST Chemistry Reference | Benzenemethanol, 4-methoxy-(105-13-5) |
| EPA Substance Registry System | 4-Methoxybenzenemethanol (105-13-5) |
| UNSPSC Code | 85151701 |
| NACRES | NA.24 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315-H317-H319 |
| GHS precautionary statements | P261-P264-P272-P280-P302+P352-P305+P351+P338 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter |
| Hazard symbols | Xn,Xi |
| Risk statements (R) | 22-36/37/38-63-62-41-37/38-20/21/22 |
| Safety statements (S) | 26-36-45-36/37/39 |
| UN transport number | UN1230 - class 3 - PG 2 - Methanol, solution |
| Water hazard class (WGK) | 1 |
| RTECS number | DO8925000 |
| Hazard Note | Irritant |
| TSCA inventory status | TSCA listed |
| Customs code | 29094990 |
| Storage class | 10 - Combustible liquids |
| Hazard class | Eye Irrit. 2Skin Irrit. 2Skin Sens. 1B |
| Toxicity | LD50 orally in rats: 1.2 ml/kg (Woodart) |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | DangerH302 (97.3%): Harmful if swallowed [Warning Acute toxicity, oral]H317 (95.5%): May cause an allergic skin reaction [Warning Sensitization, Skin]H318 (91.5%): Causes serious eye damage [Danger Serious eye damage/eye irritation]P261, P264, P264+P265, P270, P272, P280, P301+P317, P302+P352, P305+P354+P338, P317, P321, P330, P333+P317, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 2001 reports by companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatory information | Chemical: Benzenemethanol, 4-methoxy-Hazard Traits - Fragrance AllergenAuthoritative List - Annex III of the EU Cosmetics Regulation No. 1223/2009 - Fragrance AllergensReport - 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)Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Benzenemethanol, 4-methoxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenemethanol, 4-methoxy- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 03-01-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/16802Status: Active Update: 25-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/121254-Methoxybenzyl alcohol: Does not have an individual approval but may be used under an appropriate group standard |
| Other safety information | IMAP assessments - Benzenemethanol, 4-methoxy-: Human health tier II assessmentIMAP assessments - Benzenemethanol, 4-methoxy-: Environment tier I assessment |
| Hazards summary | A moderate skin irritantOral LD50 (rat) = 1,200 uL/kg[RTECS] Included in list of established contact allergens in humans[EC: Scientific Committee on Consumer Safety: Fragrance allergens in cosmetic products (2011)] Safe when used as a flavoring agent in food[JECFA] May cause serious eye injuryHarmful by ingestion[ECHA REACH Registrations] A skin and strong eye irritantToxic by ingestion[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Acute Tox. 4 (97.3%)Skin Sens. 1B (95.5%)Eye Dam. 1 (91.5%)Acute toxicity - category 4Eye irritation - category 2ASkin sensitisation - category 1 |
| Protective Action Criteria (PAC) | 4.0 [mg/m3]44 [mg/m3]260 [mg/m3] |
| Adverse effects | Skin Sensitizer - An agent that can induce an allergic reaction in the skin. |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter |
| Water hazard class (WGK) | 1 |
| TSCA inventory status | TSCA listed |
| RTECS number | DO8925000 |
| UN transport number | UN1230 - class 3 - PG 2 - Methanol, solution |
| Customs code | 29094990 |
| Toxicity | LD50 orally in rats: 1.2 ml/kg (Woodart) |
| Risk statements (R) | 22-36/37/38-63-62-41-37/38-20/21/22 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xn,Xi |
| hazard_note | Irritant |
| Safety statements (S) | 26-36-45-36/37/39 |
| Storage class | 10 - Combustible liquids |
| GHS hazard statements | H315-H317-H319 |
| REACH registrations | Active |
| Hazard class | Eye Irrit. 2Skin Irrit. 2Skin Sens. 1B |
| GHS precautionary statements | P261-P264-P272-P280-P302+P352-P305+P351+P338 |
Applications & Uses
Uses
1. 4-Methoxybenzyl alcohol mainly used in floral flavor with fragrance flavor, such as hawthorn flowers, jasmine, acacia, shy flowers, acacia, lilac, lily of the valley, violet, magnolia, sunflower, daffodils and so on. It can also be used for the need for chypre spices with vanilla flavor to coordinate the aroma and increase the aroma of beans. It can also be used for chocolate, cocoa and fresh fruit flavor. 2. GB 2760-1996 provides as allowable food flavors. It is mainly used for the preparation of vanilla, chocolate, cocoa, almonds, peaches and other flavor. 3. It is used for the preparation of drugs and spices. 4. It is used as pharmaceutical intermediates. 5. 4-Methoxybenzyl alcohol has a slightly sweet aroma of anise, commonly used in the preparation of jasmine, lilac and other flavors, suitable for deployment of perfume. The goods are allowable food spices provided in China's GB2760-86. It is mainly used to formulate the flavor of vanilla, chocolate, cocoa, almonds and peaches. It can also be used in organic synthesis and as a solvent. 6. It is used as moxonidine intermediates. 7. It is alcohol synthesis spices. It is mainly used as the blending spices of jasmine, cloves, fragrant peas, gardenia and other flavors for perfume and other cosmetics. 8. It can provide the temporary protection for the carbohydrate anti-OH-group.
Occurrence
Reported found in anise (Pimpinella anisum L.), honey, Bourbon vanilla (Vanilla planifolia Andrews), Tahiti vanilla (Vanilla tahitensis Moore), Illicium verum and tomato.
Uses
4-Methoxybenzyl Alcohol is used in the preparation of semiconductors, nanosheets and nanocrystals. Also is used as a reagent for various chemical organic reactions such as in the synthesis of quinolines. It is used as a fragrance and flavorant. It is used to study the photo catalytic oxidation of 4-methoxybenzyl alcohol to p-anisaldehyde.
Uses
4-Methoxybenzyl alcohol was used to study the photocatalytic oxidation of 4-methoxybenzyl alcohol to p-anisaldehyde.
General Description
Anisyl alcohol is a volatile aromatic compound mainly found in vanilla extracts and anise oil. It is used as a flavoring agent and fragrance ingredient.
Preparation & Synthesis
Preparation
By reduction from anisic aldehyde