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)

vapor pressure 

2.26hPa at 25℃

refractive index 

n20/D 1.44(lit.)

FEMA 

2563 | CIS-3-HEXENOL

Flash point:

112 °F

storage temp. 

Flammables area

solubility 

DMSO: 100 mg/mL (998.40 mM)

pka

15.00±0.10(Predicted)

form 

Liquid

color 

APHA: ≤100

Specific Gravity

0.848 (20/4℃)

Odor

at 10.00 % in dipropylene glycol. fresh green cut grass foliage vegetable herbal oily

Odor Type

green

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.

LogP

1 at 35℃

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)

Safety Information

Hazard Codes 

F

Risk Statements 

10

Safety Statements 

16

RIDADR 

UN 1987 3/PG 3

WGK Germany 

1

RTECS 

MP8400000

F 

10

TSCA 

Yes

HazardClass 

3

PackingGroup 

III

HS Code 

29052990

Hazardous Substances Data

928-96-1(Hazardous Substances Data)

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

• Language:English Provider:Leaf alcohol
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

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

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.

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.

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

Uses

cis-3-Hexen-1-ol is a naturally occuring compound that has the smell of freshly cut grass and is used to obtain a тАЬgreenтАЭ taste/smell in certain flavours and fragrances.

Definition

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

Preparation

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

Aroma threshold values

Detection: 70 ppb

Taste threshold values

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

General Description

cis-3-Hexen-1-ol is one of the key volatile constituents of green leaf volatiles(GLV) that can act as an attractant to various insects. It is emitted by green plants when they are physically damaged.

Flammability and Explosibility

Flammable

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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