2-Methoxybenzaldehyde
2-METHOXYBENZALDEHYDE · O-METHOXYBENZALDEHYDE · ortho-anisaldehyde · 2-ANISALDEHYDE · o-Anisaldehyde, 98% 100GR · o-Anisaldehyde：2-Methoxybenzaldehyde · Nc 064 · Nsc 58960
Identifiers & Physical Properties
| CAS No. | 135-02-4 |
|---|---|
| Molecular formula | C8H8O2 |
| Average molar mass | 136.15 g/mol |
| Monoisotopic mass | 136.0524295 g/mol |
| SMILES | COc1ccccc1C=O |
| InChIKey | PKZJLOCLABXVMC-UHFFFAOYSA-N |
| PubChem CID | 8658 |
| ChEMBL | CHEMBL396295 |
| ChEBI | CHEBI:172139 |
| EC No. | 205-171-7 |
| DTXSID | DTXSID1051690 |
Chemical & Physical Properties
| XLogP | 1.7 |
|---|---|
| Topological polar surface area | 26.3 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 2 |
| Heavy atoms | 10 |
| Formal charge | 0 |
| Complexity | 112 |
| Chemical classes | Other Classes -> Benzaldehydes |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| Fragrances | Fragrance Ingredient (o-Methoxybenzaldehyde) -> IFRA transparency List |
| LogP (partition coefficient) | 1.72 |
| Food additives | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Flavoring agents | EU Flavoring substances |
| Solubility | Soluble in water and propylene glycolSoluble (in ethanol)Solubility Slightly soluble in watersoluble in ethanolinsoluble |
| Boiling point | 238.00 °C. @ 760.00 mm Hg238 °C(lit.) |
| Melting point | 39 °C34-40 °C(lit.) |
| Vapor pressure | 0.12 [mmHg] |
| Physical Description | Light yellow solidified mass or fragmentsmp = 34-40 deg C[Sigma-Aldrich MSDS]Light yellow solidSweet powdery hawthorn, vanilla and almond aroma |
| Ionization Efficiency | Positive1.182.7Agilent XCTElectrospray ionizationformic acid (5.3nM) |
| Density | 1.127 g/mL at 25 °C(lit.) |
| Refractive index | 1.5608 |
| FEMA | 4077 | O-ANISALDEHYDE |
| FLAVIS Number | 05.129 | 2-Methoxybenzaldehyde |
| Flash point | 244 °F |
| Storage conditions | 2-8°C |
| Physical state | Low Melting Crystalline Mass |
| Color | Light yellow to pale brown |
| Specific gravity | 1.127 |
| PH Range | Non1 uorescence (3.1) to green 1 uorescence (4.4) |
| Odor | at 10.00 % in propylene glycol. sweet powdery hawthorn guaiacol vanilla acetophenone almond |
| Odor type | anisic |
| Biological source | synthetic |
| Sensitivity | Air Sensitive |
| JECFA Number | 2062 |
| BRN | 606301 |
| Henry's law constant | 1.0×101 mol/(m3Pa) at 25℃, Ji et al. (2008) |
| Major applications | Battery, hair dyes, bird repellents, cosmetics, antibacterial, antipyretic |
| Cosmetics Ingredients Functions | PERFUMING |
| InChI | 1S/C8H8O2/c1-10-8-5-3-2-4-7(8)6-9/h2-6H,1H3 |
| InChIKey | PKZJLOCLABXVMC-UHFFFAOYSA-N |
| SMILES | [H]C(=O)c1ccccc1OC |
| LogP (partition coefficient) | 1.72 |
| Substances Added to Food (formerly EAFUS) | O-METHOXYBENZALDEHYDE |
| FDA 21 CFR | 172.515 |
| CAS DataBase Reference | 135-02-4(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | 7CP821WF2W |
| NIST Chemistry Reference | Benzaldehyde, 2-methoxy-(135-02-4) |
| EPA Substance Registry System | Benzaldehyde, 2-methoxy- (135-02-4) |
| UNSPSC Code | 41116107 |
| NACRES | NA.24 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315-H319-H335 |
| GHS precautionary statements | P261-P264-P271-P280-P302+P352-P305+P351+P338 |
| Target organs | Respiratory system |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Hazard symbols | Xi |
| Risk statements (R) | 36/37/38-36/38 |
| Safety statements (S) | 26-36-37/39 |
| Water hazard class (WGK) | 2 |
| RTECS number | BZ2610000 |
| F | 9-23 |
| TSCA inventory status | TSCA listed |
| Customs code | 29124900 |
| Storage class | 11 - Combustible Solids |
| Hazard class | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
| Toxicity | LD50 orally in Rabbit: 2500 mg/kg LD50 dermal Rabbit > 5000 mg/kg |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 0.2% (3 of 1457) of reports.WarningH315 (99.8%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1457 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | Chemical: Benzaldehyde, 2-methoxy-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)2-Methoxybenzaldehyde: Does not have an individual approval but may be used under an appropriate group standard |
| Other safety information | IMAP assessments - Benzaldehyde, 2-methoxy-: Human health tier I assessment |
| Hazards summary | Causes lacrimation, somnolence, and changes in salivary glands in oral lethal-dose studies of mice[RTECS] An irritant[Sigma-Aldrich MSDS] See Benzaldehyde. |
| Hazard Classes and Categories | Skin Irrit. 2 (99.8%) |
| F | 9-23 |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Water hazard class (WGK) | 2 |
| TSCA inventory status | TSCA listed |
| RTECS number | BZ2610000 |
| Customs code | 29124900 |
| Toxicity | LD50 orally in Rabbit: 2500 mg/kg LD50 dermal Rabbit > 5000 mg/kg |
| Risk statements (R) | 36/37/38-36/38 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xi |
| Safety statements (S) | 26-36-37/39 |
| Storage class | 11 - Combustible Solids |
| Target organs | Respiratory system |
| GHS hazard statements | H315-H319-H335 |
| Hazard class | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
| GHS precautionary statements | P261-P264-P271-P280-P302+P352-P305+P351+P338 |
Applications & Uses
Description
O-Anisaldehyde (also 2-methoxybenzaldehyde) is found in cassia oil, cinnamon bark, and cinnamon bark oil. It is a clear colorless liquid with a strong aroma. O-Anisaldehyde is used as a flavor agent in foods including nonalcoholic/alcoholic beverages, baked goods, chewing gum, confections, frozen dairy, fruit ices, hard/soft candy, instant coffee, tea, Jams, jellies, and milk products. O-Anisaldehyde has been used to examine the acaricidal activity of Periploca sepium oil and its active component against Tyrophagus and to obtain good enantioselectivities using Cu(OAc)(2)-bis(oxazolines) via hydrogen bonding in asymmetric Henry reaction.
Description
o-Methoxybenzaldehyde has a faint, sweet, floral odor. It blends well with cassia. It has a spice-like flavor, quite bitter above 30 - 40 ppm. May be prepared from salicylaldehyde and dimethyl sulfate in weak alkaline solution.
Occurrence
Reported found in Cassia oil, cinnamon bark, and Cinnamon bark oil (Cinnamomum zeylanicum Blume), Sri Lanka (0.09–0.15%)
Uses
2-Methoxybenzaldehyde has been used to examine the acaricidal activity of Periploca sepium oil and its active component against Tyrophagus. It has also been used to obtain good enantioselectivities using Cu(OAc)(2)-bis(oxazolines) via hydrogen bonding in asymmetric Henry reaction.
Uses
2-Methoxybenzaldehyde has been used to obtain good enantioselectivities using Cu(OAc)(2)-bis(oxazolines) via hydrogen bonding in asymmetric Henry reaction.
Uses
Intermediate.