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Leaf alcohol

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Leaf alcohol Basic information
Leaf alcohol Chemical Properties
  • Melting point:22.55°C (estimate)
  • Boiling point:156-157 °C(lit.)
  • Density 0.848 g/mL at 25 °C(lit.)
  • vapor density 3.45 (vs air)
  • refractive index n20/D 1.44(lit.)
  • FEMA 2563 | CIS-3-HEXENOL
  • Flash point:112 °F
  • storage temp. Flammables area
  • form Liquid
  • pka15.00±0.10(Predicted)
  • color APHA: ≤100
  • Specific Gravity0.848 (20/4℃)
  • Water Solubility INSOLUBLE
  • Merck 14,4700
  • JECFA Number315
  • BRN 1719712
  • Stability:Stable. Substances to be avoided include strong oxidizing agents and strong acids. Flammable.
  • CAS DataBase Reference928-96-1(CAS DataBase Reference)
  • NIST Chemistry Reference3-Hexen-1-ol, (Z)-(928-96-1)
  • EPA Substance Registry System(Z)-3-Hexen-1-ol (928-96-1)
Safety Information
  • Hazard Codes F
  • Risk Statements 10
  • Safety Statements 16
  • RIDADR UN 1987 3/PG 3
  • WGK Germany 1
  • RTECS MP8400000
  • 10
  • TSCA Yes
  • HazardClass 3
  • PackingGroup III
  • HS Code 29052990
  • ToxicityThe 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).
MSDS
Leaf alcohol Usage And Synthesis
  • DescriptionLeaf alcohol exists as a liquid at room temperature with a characteristic odor of green leaves. It is found in green tea, violet leaf oil, and many types of leaves, herbs, and grasses. Leaf alcohol finds applications in perfumery as floral fragrance. Leaf alcohol is also investigated for its antidiabetic activity.
  • Chemical Propertiescolourless liquid
  • Chemical PropertiesLeaf Alcohol is a colorless liquid with the characteristic odor of freshly cut grass. In small quantities, leaf alcohol occurs in the green parts of nearly all plants. The volatile flavor constituents of green tea contain up to 30%.
    A stereospecific synthesis of (Z)-3-hexen-1-ol starts with the ethylation of sodium acetylide to 1-butyne, which is reacted with ethylene oxide to give 3-hexyn-1-ol. Selective hydrogenation of the triple bond in the presence of palladium catalysts yields (Z)-3-hexen-1-ol. Biotechnological processes have been developed for its synthesis as a natural flavor compound, for example.
    Leaf alcohol is used to obtain natural green top notes in perfumes and flavors. In addition, it is the starting material for the synthesis of (2E,6Z)-2,6-nonadien-l-ol and (2E,6Z)-2,6-nonadien-l-al.
  • Chemical Propertiescis-3-Hexen-l-ol has an intense, green odor, not as strong as the corresponding aldehyde and a characteristic herbaceous, leafy odor on dilution. This substance can be obtained through extraction from various essential oils and purified by reacting it to the corresponding phthalate or allophanate; it was synthesized by Ruzicka and Schinz, who also clarified its chemical structure; Stoll and Rouve reported on the most significant differences between the natural and the synthetic products.
  • Chemical Properties3-Hexen-1-ol has an intense, grassy-green odor, not as strong as the corresponding aldehyde, and a characteristic herbaceous, leafy odor on dilution.
  • OccurrenceMain constituent of the oil distilled from the infusion of fermented tea leaves. Reported found as the corresponding ester of phenylacetic acid in the oil of Japanese mint (Mentha arvensis); the volatile oil of Thea chinensis contains approximately 26 to 35% 3-hexen-1-ol, whereas larger amounts are reported in the oils of Morus bombysic, Robinia pseudacacia and Raphanus sativus. Probably occurring also in several green leaves and herbs; reported found in the fruit juices of raspberry, grapefruit and others. Also reported in over 200 foods including apple, apricot, banana, citrus peel oils and juices, berries, guava, mango, grapes, pineapple, cabbage, kohlrabi, celery, cucumber, lettuce, leek, peas, sauerkraut, tomato, ginger, peppermint oil, coconut oil, spearmint oil, mustard, parsley, breads, butter, fish, fish oil, cognac, brandy, cider, sherry, grape wines, tea, soybeans, avocado, olive, passion fruit, plum, rose apple, Malay apple, water apple (Syzigium spp.), beans, marjoram, starfruit, broccoli, pear and apple brandies, figs, brussels sprouts, radish, prickly pear, litchi, dill, lovage, pumpkin, corn oil, malt, laurel, kiwifruit and other sources
  • PreparationBy the reaction of butyne-1 with ethylene oxide and subsequent selective reduction to the eis isomer (Bedoukian, 1967).
  • DefinitionChEBI: A primary alcohol that consists of (3Z)-hex-3-ene substituted by a hydroxy group at position 1.
  • Aroma threshold valuesDetection: 70 ppb
  • Taste threshold valuesTaste characteristics at 30 ppm: fresh, green, raw fruity with a pungent depth
  • Chemical SynthesisExtracted from various essential oils and purified by reacting it to the corresponding phthalate or allophanate; it was synthesized by Ruzi-ka and Schinz, who also clarified its chemical structure; Stoll and Rouve reported on the most significant differences between the natural and the synthetic products (Burdock, 1995)
  • References[1] NPCS Board of Consultants & Engineers, Industrial Alcohol of Technology Handbook, 2010
    [2] A. Shirwaikar, K. Rajendran and C. Kumar, Oral Antidiabetic Activity of Annona squamosa Leaf Alcohol Extract in NIDDM Rats, Pharmaceutical Biology, 2004, vol. 42, 30-35
Leaf alcohol Preparation Products And Raw materials
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