28069-72-9 Usage
Description
TRANS,CIS-2,6-NONADIEN-1-OL, also known as (2E,6Z)-2,6-Nonadien-1-ol, is a clear colorless liquid with an intense, heavy, fatty, green odor, reminiscent of violet leaves. It is a powerful fragrance substance that occurs naturally in cucumber oil, violet leaf oil, and violet blossom oil. The starting material for its synthesis is (Z)-3-hexen-1-ol, which is converted via its halide into the corresponding Grignard reagent. The Grignard reagent is then reacted with acrolein to give 1,6-nonadien-3-ol, which is converted into (2E,6Z)-2,6-nonadien-1-ol by allylic rearrangement.
Uses
Used in Personal Care Products:
TRANS,CIS-2,6-NONADIEN-1-OL is used as an antimicrobial composition for personal care products, providing protection against harmful microorganisms and ensuring the safety and efficacy of these products.
Used in Food Industry:
TRANS,CIS-2,6-NONADIEN-1-OL is used as a natural product and food additive, enhancing the flavor and aroma of various food items.
Used in Fragrance Industry:
TRANS,CIS-2,6-NONADIEN-1-OL is used as a fragrance substance in fine fragrances to create refined violet odors and to impart interesting notes to other blossom compositions.
Used in Aroma Compositions:
TRANS,CIS-2,6-NONADIEN-1-OL is used in aroma compositions for fresh, green cucumber notes, adding a unique and appealing scent to various products.
Synthesis Reference(s)
Synthesis, p. 528, 1978 DOI: 10.1055/s-1978-24798
Safety Profile
Low toxicity by
ingestion and skin contact. A skin irritant.
When heated to decomposition it emits
acrid smoke and irritating fumes.
Check Digit Verification of cas no
The CAS Registry Mumber 28069-72-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,8,0,6 and 9 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 28069-72:
(7*2)+(6*8)+(5*0)+(4*6)+(3*9)+(2*7)+(1*2)=129
129 % 10 = 9
So 28069-72-9 is a valid CAS Registry Number.
InChI:InChI=1/C9H16O/c1-2-3-4-5-6-7-8-9-10/h3-4,7-8,10H,2,5-6,9H2,1H3/b4-3-,8-7+
28069-72-9Relevant articles and documents
Tandem catalysis in the polycyclisation of dienes to produce multi-substituted tetrahydrofurans
Donohoe, Timothy J.,Lindsay-Scott, Peter J.,Parker, Jeremy S.
scheme or table, p. 3523 - 3526 (2009/10/26)
A new catalytic protocol has been established by using two separate oxidation reactions, catalysed by osmium, in tandem. Control of the pH and oxidation state of the metal is crucial in controlling this new sequence, which begins with a tethered aminohydr
A New Synthesis of Nona-2E,6Z-dienal
Vig, O. P.,Sharma, M. L.,Gauba, Rita
, p. 313 - 314 (2007/10/02)
Monosodio ethyl malonate on alkylation with 1-bromo-pent-2-yne (III) furnishes the diester (IV) which on decarbethoxylation with NaCl/DMSO, followed by LAH/EtOH reduction of the resultant ester (V), yields the carbinol (VI).Hydrogenation of VI in the presence of Lindlar's catalyst produces hept-4Z-en-1-ol (VII), which on pyridinium chlorochromate oxidation gives the aldehyde (VIII).Wittig-Horner reaction on VIII using ethyl diethylphosphonoacetate produces the dienoate (IX), which on LAH/EtOH reduction followed by oxidation with Corey's reagent, affords the title compound(I).
