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
• 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.

Watermelon Aroma-Precursor, Ester-Forming and Odor-Modulating Properties of cis-3-Nonen-1-ol

Genthner, E. R. Identification of Key Odorants in Fresh-Cut Watermelon Aroma and Structure-Odor Relationships of cis,cis-3,6-Nonadienal and Ester Analogs

The chemical composition, aroma-related properties and ester synthesis potential of cis-3-nonen-1-ol were studied using gas chromatography-mass spectrometry (GC-MS), static headspace analysis (SHA), gas chromatography-olfactometry (GCO), and in vitro esterification reactions. cis-3-nonen-1-ol is a naturally occurring C₉ unsaturated alcohol and a key intermediate in the lipoxygenase pathway of watermelon aroma biosynthesis, derived from the enzymatic oxidation of linolenic acid. It serves as the direct precursor to cis-3-nonenal (a melon rind-like odorant) via oxidation, and its structure features a cis double bond at the C-3 position of a nine-carbon aliphatic chain with a terminal hydroxyl group.
cis-3-nonen-1-ol exhibited significant aroma-precursor activity: in fresh-cut watermelon, it is rapidly converted to cis-3-nonenal (odor detection threshold = 0.3 ppb) by alcohol dehydrogenase, a reaction initiated by tissue disruption. Though cis-3-nonen-1-ol itself has a higher odor detection threshold (10 ppb) than its aldehyde derivative, it was identified as an abundant volatile component in watermelon extracts (via GC-MS) and contributes indirectly to the fruit's characteristic aroma through enzymatic transformation. It demonstrated potent ester-forming properties: via acid-catalyzed esterification or acylation reactions, it successfully formed a series of stable esters including cis-3-nonenyl formate, acetate, propionate, and butyrate, as well as carboxylic acid esters (methyl, ethyl, propyl, butyl cis-3-nonenoate). These esters exhibited structure-dependent odor characteristics: cis-3-nonenyl formate was described as "green apple, slightly sweet, and berry-like," while cis-3-nonenyl acetate had "orange peel, pear, and green" notes, and methyl cis-3-nonenoate featured "pineapple, melon, and creamy" aromas. Additionally, cis-3-nonen-1-ol showed odor-modulating effects through structural variations: moving the cis double bond or modifying the terminal functional group (hydroxyl to ester) altered odor thresholds and sensory profiles, with alcohol esters consistently displaying lower thresholds than corresponding carboxylic acid esters. These studies demonstrate that cis-3-nonen-1-ol possesses significant watermelon aroma-precursor, ester-forming, and odor-modulating properties.
The in vitro aroma-precursor and ester-forming effects were investigated via SHA and GCO of fresh-cut watermelon headspace (1 minute post-cutting) to track conversion to cis-3-nonenal. Ester synthesis was conducted using formic/acetic/propionic/butyric acids (for alcohol esters) or methanol/ethanol/propanol/butanol (for carboxylic acid esters) with acid catalysis (sulfuric acid) or acylation (acetyl/propionyl/butyryl chloride + triethylamine). Synthesized esters were purified and characterized by GC-MS (retention indices, mass spectra) and sensory evaluation (odor description, relative threshold determination via GCO). The results verified that cis-3-nonen-1-ol is a critical intermediate in watermelon aroma biosynthesis and a versatile precursor for stable, fruity esters with potential applications as flavoring agents.

Cantaloupe Aroma-Contributing, Enzyme-Responsive and Prebiotic-Enhancing Properties of cis-3-Nonen-1-ol

Nattaporn, W., & Pranee, A. Effect of pectinase on volatile and functional bioactive compounds in the flesh and placenta of 'Sunlady' cantaloupe. International Food Research Journal, 18 (2011): 819-827.

The chemical composition, aroma characteristics and functional properties of cis-3-nonen-1-ol were studied using solid-phase microextraction (SPME), gas chromatography-mass spectrometry (GC-MS), and in vitro enzymatic degradation assays. cis-3-nonen-1-ol is a C₉ unsaturated alcohol with a characteristic "melon-like" aroma, identified as a key volatile compound in the placenta of fully ripe 'Sunlady' cantaloupe (Cucumis melo var. cantalupensis). It is released from plant cell walls via the hydrolysis of polysaccharides (pectin, cellulose, hemicellulose) by pectinase enzymes, contributing to the fruity and herbal flavor profile of cantaloupe.
cis-3-nonen-1-ol exhibited significant cantaloupe aroma-contributing activity: it was exclusively detected in pectinase-degraded cantaloupe placenta (sample P5) but not in undegraded control samples (P0), confirming its enzyme-dependent release from cell wall matrices. As a volatile alcohol, it contributes a "fatty, green herbal" flavor note that complements other key cantaloupe volatiles (e.g., nonanal, cis-6-nonen-1-ol, ethyl acetate) to form the fruit's characteristic fragrance. It demonstrated enzyme-responsive release properties: treatment with commercial pectinase (Pectinex® Ultra SP-L) at optimal conditions (3.0% v/w enzyme concentration, 6 h degradation time) led to a marked increase in total volatile compounds in cantaloupe placenta (21 types in P5 vs. 18 types in P0), with cis-3-nonen-1-ol emerging as a major component. Additionally, cis-3-nonen-1-ol was associated with enhanced prebiotic activity: pectinase-degraded cantaloupe placenta (P5) containing cis-3-nonen-1-ol showed a prebiotic activity score of 0.14 for Lactobacillus acidophilus La5 and 0.33 for Bifidobacterium lactis Bb12, promoting the growth of probiotic bacteria while inhibiting pathogenic Escherichia coli. These studies demonstrate that cis-3-nonen-1-ol possesses significant cantaloupe aroma-contributing, enzyme-responsive, and prebiotic-enhancing properties.
The in vitro aroma-contributing and enzyme-responsive effects were investigated using SPME-GC-MS to analyze volatile compounds in cantaloupe flesh and placenta (fresh mass, FM) before and after pectinase treatment. Enzymatic degradation was optimized by monitoring reducing sugar content (39.12-40.44 mg glucose/g FM for placenta) and bioactive compound release. Prebiotic activity was evaluated by measuring the growth of probiotic strains (L. acidophilus La5, B. lactis Bb12) and pathogenic E. coli in media supplemented with pectinase-degraded cantaloupe samples, with activity scores calculated relative to glucose controls. The results verified that cis-3-nonen-1-ol is a critical enzyme-released volatile that enhances both the sensory and functional value of cantaloupe.

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.