cis-3-Nonen-1-ol

• CAS: 10340-23-5
• Catalog Number: ACM10340235
• Category: Other Products; Main Products
• Molecular Weight: 142.24g/mol
• Molecular Formula: C9H18O
• Description: Clear colourless liquid; waxy green melon aroma
• Synonyms: cis-3-Nonen-1-ol;(Z)-Non-3-en-1-ol;(Z)-3-nonen-1-ol;3-Nonen-1-ol, (Z)-;10340-23-5;(3Z)-3-Nonen-1-ol;UNII-W8G7341QJ8;(z)-3-nonenol;3Z-Nonen-1-ol;W8G7341QJ8;MFCD00010314;EINECS 233-735-2;3(Z)?-?Nonenol;Z-non-3-en-1-ol;AI3-38506;(3Z)non-3-en-1-ol;SCHEMBL82915;cis-3-Nonen-1-ol, 95%;IFTBJDZSLBRRMC-SREVYHEPSA-;DTXSID60884464;LMFA05000134;ZINC12358842;AKOS024348811;cis-3-Nonen-1-ol, 95%, stabilized;N0588;ST50823823;J-000953;Q27292461
• IUPAC Name: (Z)-non-3-en-1-ol
• Canonical SMILES: CCCCCC=CCCO
• InChI: InChI=1S/C9H18O/c1-2-3-4-5-6-7-8-9-10/h6-7,10H,2-5,8-9H2,1H3/b7-6-
• InChI Key: IFTBJDZSLBRRMC-SREVYHEPSA-N
• Melting Point: 107-109 °C
• Flash Point: 62 °C
• Density: 0.841-0.849 (20º)
• Solubility: Practically insoluble to insoluble in water;Soluble (in ethanol)
• Appearance: Colorless liquid
• Complexity: 76.8
• Covalently-Bonded Unit Count: 1
• EC Number: 233-735-2
• Exact Mass: 142.135765193g/mol
• Heavy Atom Count: 10
• Hydrogen Bond Acceptor Count: 1
• Monoisotopic Mass: 142.135765193g/mol
• Refractive Index: 1.440-1.460
• Rotatable Bond Count: 6
• Topological Polar Surface Area: 20.2Ų
• UNII: W8G7341QJ8
• XLogP3: 2.9

Case Study

Evaluation of Antibacterial and Quorum Sensing Properties of Cis-3-Nonen-1-Ol

Ahmad A, et al. Letters in applied microbiology, 2015, 60(1), 8-19.

Cis-3-Nonen-1-ol is one of the common essential oil compounds. The antibacterial and quorum sensing (QS) properties of 29 common essential oil compounds, including cis-3-Nonen-1-ol, were evaluated. The results showed that trans-3-nonen-1-ols exhibited >90% inhibition of violaceous pigments, indicating its potential as QS inhibitors.
Quantitative evaluation of anti-quorum sensing activity in C. violaceum
· To confirm the effect of these QS inhibitory compounds, their effect on AHL-mediated violacein pigment production was quantified spectrophotometrically. The minimum quorum sensing inhibitory concentrations (MQSIC) of all the compounds have been listed in table.
· As observed in the agar diffusion assay, violacein production decreased in treated vs control cells, with >50% inhibition being observed with MQSIC exposure.
· The most prominent violacein inhibition (>90%) was observed with 0.125 mg ml-1 of α-terpineol and cis-3-nonen-1-ol.

Simple Synthetic Method for Sulfenyletherification of Cis-3-Nonen-1-Ol

Gao Y, et al. Synthetic Communications, 2018, 48(21), 2773-2781.

Sulfenyletherification reactions of unsaturated alcohols with DMSO and oxalyl chloride have been successfully achieved. For example, cis-3-nonen-1-ol 1c was converted to a seven-membered cyclic acetal 2c with cis configuration in 24% yield.
Formation of the cyclic acetal from cis-3-nonen-1-ol
· First, methanechloride attacks the double bond of cis-3-alken-1-ol to undergo electrophilic addition to generate the intermediate cis-thiiranium ion stereospecifically. The severe steric interaction between R group and hydroxyl group of cis-thiiranium ion prevents hydroxyl group from approaching the carbon attached to R group so that no cyclic ether is produced.
· Then, the oxygen of carbonyl group of formaldehyde as the nucleophile approaches the carbon attached to R group from less steric side to undergo an intermolecular nucleophilic substitution on the cis-thiiranium ion ring. The carbocation intermediate obtained is captured by the intramolecular hydroxyl group and cyclized to yield the seven-membered cyclic acetal.
· The cyclic acetals are obtained with cis-configuration stereospecifically since two stereocenters are formed by a stereospecific electrophilic addition of methanesulfenyl chloride to a double bond followed by a stereospecific intramolecular nucleophilic substitution on the cis-thiiranium ion ring.

Custom Q&A

What is the molecular formula of cis-3-Nonen-1-ol?

The molecular formula of cis-3-Nonen-1-ol is C9H18O.

What are the synonyms of cis-3-Nonen-1-ol?

The synonyms of cis-3-Nonen-1-ol include (Z)-Non-3-en-1-ol, (Z)-3-nonen-1-ol, 3-Nonen-1-ol, (Z)-, 3-Nonen-1-ol, (3Z)-, 3Z-Nonen-1-ol, (3Z)-3-Nonen-1-ol, (z)-3-nonenol, 3(Z)-Nonenol, UNII-W8G7341QJ8, W8G7341QJ8, EINECS 233-735-2, AI3-38506, cis-3-Nonenol, Z-non-3-en-1-ol, SCHEMBL82915, (3Z)-non-3-en-1-ol, cis-3-Nonen-1-ol, 95%, FEMA NO. 4412, 3-NONEN-1-OL, CIS-, IFTBJDZSLBRRMC-SREVYHEPSA-, DTXSID60884464, CHEBI:179599, CIS-3-NONEN-1-OL [FHFI], LMFA05000134, MFCD00010314, AKOS024348811, cis-3-Nonen-1-ol, 95%, stabilized, HY-W127320, BS-48915, CS-0185562, N0588, EN300-306425, J-000953, Q27292461.

What is the InChI of cis-3-Nonen-1-ol?

The InChI of cis-3-Nonen-1-ol is InChI=1S/C9H18O/c1-2-3-4-5-6-7-8-9-10/h6-7,10H,2-5,8-9H2,1H3/b7-6-.

What is the molecular weight of cis-3-Nonen-1-ol?

The molecular weight of cis-3-Nonen-1-ol is 142.24g/mol.

How many rotatable bonds does cis-3-Nonen-1-ol have?

cis-3-Nonen-1-ol has 6 rotatable bonds.

What is the topological polar surface area of cis-3-Nonen-1-ol?

The topological polar surface area of cis-3-Nonen-1-ol is 20.2Ų.

Does cis-3-Nonen-1-ol have any hydrogen bond donor count?

Yes, cis-3-Nonen-1-ol has 1 hydrogen bond donor count.

What is the CAS number of cis-3-Nonen-1-ol?

The CAS number of cis-3-Nonen-1-ol is 10340-23-5.

Is cis-3-Nonen-1-ol an irritant?

Yes, cis-3-Nonen-1-ol is classified as an irritant.

What is the density of cis-3-Nonen-1-ol?

The reference does not provide information about the density of cis-3-Nonen-1-ol.

Synthetic Use

Upstream Synthesis Route 1

• 31333-13-8

• 10340-23-5

Reference: [1]Stoller; Mioskowski; Millet; Sepulchre; Bellamy
[Tetrahedron Letters, 1990, vol. 31, # 35, p. 5035 - 5038]

Upstream Synthesis Route 2

• 31333-13-8

• 10340-23-5
• 10339-61-4

Reference: [1]Tour, James M.; Pendalwar, Shekhar L.; Kafka, Cynthia M.; Cooper, Joel P.
[Journal of Organic Chemistry, 1992, vol. 57, # 18, p. 4786 - 4787]

Downstream Synthesis Route 1

• 10340-23-5
• 98-59-9

• 72297-08-6

Reference: [1]Cohen; Banner; Lopresti; et al.
[Journal of the American Chemical Society, 1983, vol. 105, # 11, p. 3661 - 3672]
[2]Hayes, Jerome F.; Shipman, Michael; Twin, Heather
[Journal of Organic Chemistry, 2002, vol. 67, # 3, p. 935 - 942]
[3]Corey,E.J. et al.
[Journal of the American Chemical Society, 1979, vol. 101, # 22, p. 6748 - 6749]

* For details of the synthesis route, please refer to the original source to ensure accuracy.