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Leaf alcohol

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Leaf alcohol Basic information

Product Name:
Leaf alcohol
CAS:
928-96-1
MF:
C6H12O
MW:
100.16
EINECS:
213-192-8
Mol File:
928-96-1.mol
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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
pka
15.00±0.10(Predicted)
color 
APHA: ≤100
Specific Gravity
0.848 (20/4℃)
Water Solubility 
INSOLUBLE
Merck 
14,4700
JECFA Number
315
BRN 
1719712
Stability:
Stable. Substances to be avoided include strong oxidizing agents and strong acids. Flammable.
CAS DataBase Reference
928-96-1(CAS DataBase Reference)
NIST Chemistry Reference
3-Hexen-1-ol, (Z)-(928-96-1)
EPA Substance Registry System
(Z)-3-Hexen-1-ol (928-96-1)
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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
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).

MSDS

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Leaf alcohol Usage And Synthesis

Description

Leaf 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 Properties

colourless liquid

Chemical Properties

Leaf 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 Properties

cis-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 Properties

3-Hexen-1-ol has an intense, grassy-green odor, not as strong as the corresponding aldehyde, and a characteristic herbaceous, leafy odor on dilution.

Occurrence

Main 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

Preparation

By the reaction of butyne-1 with ethylene oxide and subsequent selective reduction to the eis isomer (Bedoukian, 1967).

Definition

ChEBI: A primary alcohol that consists of (3Z)-hex-3-ene substituted by a hydroxy group at position 1.

Aroma threshold values

Detection: 70 ppb

Taste threshold values

Taste characteristics at 30 ppm: fresh, green, raw fruity with a pungent depth

Chemical Synthesis

Extracted 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

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