C3 LEAF ALCOHOL
cis-3-Hexen-1-ol
CAS: 928-96-1
Molecular Formula: C6H12O
C3 LEAF ALCOHOL - Names and Identifiers
C3 LEAF ALCOHOL - Physico-chemical Properties
| Molecular Formula | C6H12O |
| Molar Mass | 100.16 |
| Density | 0.848g/mLat 25°C(lit.) |
| Melting Point | 22.55°C (estimate) |
| Boling Point | 156-157°C(lit.) |
| Flash Point | 112°F |
| JECFA Number | 315 |
| Water Solubility | INSOLUBLE |
| Vapor Presure | 2.26hPa at 25℃ |
| Vapor Density | 3.45 (vs air) |
| Appearance | Transparent, colorless liquid |
| Specific Gravity | 0.848 (20/4℃) |
| Color | APHA: ≤100 |
| Merck | 14,4700 |
| BRN | 1719712 |
| pKa | 15.00±0.10(Predicted) |
| Storage Condition | Flammables area |
| Stability | Stable. Substances to be avoided include strong oxidizing agents and strong acids. Flammable. |
| Sensitive | Sensitive to light |
| Refractive Index | n20/D 1.44(lit.) |
| MDL | MFCD00063217 |
| Physical and Chemical Properties | Colorless oily liquid. It has strong grass aroma and new tea flavor. Boiling point 156 ℃, flash point 44 ℃. Soluble in ethanol, propylene glycol and most non-volatile oils, very slightly soluble in water. Natural products exist in tea: mint, jasmine, grapes, raspberries, grapefruit, etc. |
| Use | N-3-hexenol is also known as leaf alcohol. It is not only commonly used in daily chemical flavors with floral fragrance, but also used in edible flavors with fruity and mint fragrance. It can be used to activate floral, fruity and mint fragrance. Head in daily chemical and edible flavors. |
C3 LEAF ALCOHOL - Risk and Safety
| Hazard Symbols | F - Flammable |
| Risk Codes | 10 - Flammable |
| Safety Description | 16 - Keep away from sources of ignition. |
| UN IDs | UN 1987 3/PG 3 |
| WGK Germany | 1 |
| RTECS | MP8400000 |
| FLUKA BRAND F CODES | 10 |
| TSCA | Yes |
| HS Code | 29052990 |
| Hazard Class | 3 |
| Packing Group | III |
| Toxicity | The acute oral LD50 value in rats was reported as 4.70 g/kg (3.82-5.58 g/kg) (Moreno, 1973). The acute dermal LD50 value in rabbits was reported as > 5 g/kg (Moreno, 1973). |
C3 LEAF ALCOHOL - Introduction
There are strong, fresh and strong green incense and grass incense. Insoluble in water, soluble in ethanol and propylene glycol, miscible with oil.
Last Update：2022-10-16 17:30:12
C3 LEAF ALCOHOL - Reference Information
| FEMA | 2563 | CIS-3-HEXENOL |
| LogP | 1 at 35℃ |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Introduction | leaf alcohol is one of the important spices of flower-type and cyan-type flavor, and only about 1% of fresh Qingye fragrance can be obtained. Under the slogan of returning to nature, leaf alcohol will play an important role in the western type essence. In the melon and fruit flavor is effective only in trace amounts. A perfume compound that is a colorless liquid with an elegant aroma of green leaves. Slightly soluble in water, soluble in ethanol, propylene glycol and other organic solvents, often exist in the form of alcohol or ester in tea, tomato, osmanthus, Jasmine, fragrant leaves, mint, Violet and many other plants. Its synthetic route reported a lot, the Japanese high sand spice company to pentadiene and formaldehyde as raw material, Mr. into dihydropyran, and then under the catalysis of lithium ring opening and get. |
| Application | leaf alcohol is widely distributed in the leaves, flowers and fruits of green plants, thus, it has been taken up by the human body with the food chain since the history of human beings. China's GB2760-1996 standard can be used for food flavor according to the production needs. In Japan, leaf alcohol is widely used in the preparation of natural fresh flavor flavors such as banana, strawberry, citrus, Rose grape and apple, and also used in combination with acetic acid, valeric acid, lactic acid and other esters, to change the taste of food, mainly used to suppress the sweet aftertaste of cool drinks and fruit juice. 2. Application of leaf alcohol in daily chemical industry leaf alcohol has strong fresh grass aroma, is a popular fragrance of precious spices. Leaf alcohol and its esters are indispensable flavoring agents in flavor production. It is reported that at present, more than 40 famous flavor formulas in the world all contain leaf alcohol, usually only need to add 0.5% or less leaf alcohol, can get significant leaf green aroma. In the cosmetics industry, leaf alcohol is used to prepare a variety of artificial essential oils similar to natural spices, such as Lily of the valley, clove, oak, mint and lavender essential oils, etc, it can also be used to prepare a variety of floral essences, so that the artificial essential oils and essences have the fragrance of the head. Leaf alcohol is also an important raw material for the synthesis of methyl jasmonate and methyl jasmonate. Leaf alcohol and its derivatives are symbols of the Green Revolution of the spice industry in the 60s of the 20th century. 3. Application of leaf alcohol in biological control leaf alcohol is also an indispensable physiological active substance in both plants and insects. Insects use leaf alcohol as an alarm, collection and other pheromones or sex hormones. Such as leaf alcohol and benzene after mixing in a certain proportion, can induce the aggregation of male scab, Beetle, so as to kill such forest pests in a large area. It can be seen that leaf alcohol is a compound with important application value. |
| synthesis method | 3-hexyn-1-ol is reacted with hydrogen in the presence of Lindlar catalyst, the hydrogenation of the alkyne can be retained in the olefin stage and the cis configuration can be obtained. This method is one of the most important methods for the preparation of leaf alcohol. Among them, Japan has made a breakthrough in this route and has been applied to industrial production. They used the basic raw materials in petrochemical products butyne or butadiene and ethylene oxide in the metal sodium and liquid ammonia in the first key intermediate 3-hexyne -1-alcohol, and then control the catalytic hydrogenation to obtain leaf alcohol. Under the synthetic route: |
| content analysis | The total amount of each isomer and the content of the main component were analyzed by gas chromatography using a polar column in GT-10-4. |
| toxicity | GRAS(FEMA). LD50 4700 mg/kg (rat, oral). |
| usage limit | FEMA(mg/kg): Soft drink 1.0; Cold drink 3.7; Candy 5.0; Baked goods 5.0. Moderate limits (FDA § 172.515,2000). |
| Use | GB 2760-96 specifies the permitted use of flavorants. Mainly used to prepare a variety of fruits and mint-type flavor. cis-3-hexenol has a flavor similar to isoamyl alcohol and is used to make advanced flavors; Trans -3-hexenol has a strong grass flavor in a very dilute state and is used in the production of specialty flavors. n-3-hexenol, also known as leaf alcohol, is not only commonly used in daily flavor with flower fragrance, but also used in edible flavor with fruit flavor and mint flavor, which can be used to activate flower flavor, fruit aroma and mint aroma in daily chemical and food flavor. |
| production method | lithium metal (or sodium metal) is reacted with acetylene in liquid ammonia to produce acetylene (or sodium acetylene), then it reacts with ethanol to produce ethyl acetylene. Ethyl acetylene was reacted with ethylene oxide to give 3-acetylen-1-ol, and finally the product was hydrogenated to give leaf alcohol. From tetrahydrofuran as starting material, or from the selective hydrogenation of 3-hexynol. It can also be formed by Wittig reaction of 3 chloropropanol, triphenylphosphine and propionaldehyde. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:52:54
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