Basic information
- CAS
502-47-6- Standard SMILES
CC(C)=CCCC(C)CC(=O)O- InChIKey
GJWSUKYXUMVMGX-UHFFFAOYSA-N- Molecular formula
- C10H18O2
- Average molar mass
- 170.25 g/mol
- Monoisotopic mass
- 170.13067982
Overview
Citronellic acid is a monounsaturated fatty acid that is oct-6-enoic acid carrying methyl groups at positions 3 and 7. It has a role as a flavouring agent and a plant metabolite. It is a monoterpenoid, a monounsaturated fatty acid and a medium-chain fatty acid. It is functionally related to a citronellal.
Names & identifiers
- Preferred name
- Citronellic acid
- IUPAC
- 3,7-dimethyloct-6-enoic acid
- English name
- CITRONELLIC ACID
- Molecular formula
- C10H18O2
- Molecular weight
- 170.25
Names & synonyms
Citronellic acid3,7-dimethyloct-6-enoic acid502-47-63,7-Dimethyl-6-octenoic acidRhodinolic acidRhodinic Acid6-OCTENOIC ACID, 3,7-DIMETHYL-FEMA No. 3142DTXSID10471061JJT408R87DTXCID9027106CHEBI:80507
Show more names
FEMA 3142TIMTEC-BB SBB006596Citronellic acid 98%Citronellic Acid >(+/-)-CITRONELLIC ACID
RefChem:577476207-939-7Citronellate57030-77-0MFCD00002728EINECS 207-939-7BRN 1722960Callitrol
Database identifiers
- CAS
502-47-6- PubChem CID
- 10402
- DTXSID
DTXSID1047106- ChEMBL
CHEMBL2288023- ChEBI
CHEBI:80507- UNII
- 1JJT408R87
- EC Number
- 207-939-7
- Nikkaji
- J11.776E
Properties
Computed structural properties
- XLogP
- 3
- Topological polar surface area
- 37.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 5
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 167
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Organic Acids
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Branched fatty acids [FA0102]
FragrancesFragrance Ingredient (3,7-Dimethyl-6-octenoic acid) -> IFRA transparency List
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density0.920-0.926 (20 °C)
Flavoring AgentsEU Flavoring substances
Solubility
slightly
Insoluble in glycerol, water; soluble in most fixed oils, propylene glycol
soluble (in ethanol)
Boiling Point
121.00 to 122.00 °C. @ 1.00 mm Hg
121-122 °C (1 mm Hg)
Melting Point257 °C
Refractive Index1.455-1.462
Physical Description
Liquid; [Sigma-Aldrich MSDS]
Solid
Colourless liquid; smokey, whisky aroma
Collision Cross Section148.8 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID1047106]
Physicochemical properties
- Boiling point
- 121 · 121-122 °C1 mm Hg(lit.)
- Density
- 0.923 g/mL · 0.923 g/mL at 25 °C(lit.)
- FEMA
- 3142 · 3142 | 3,7-DIMETHYL-6-OCTENOIC ACID
- refractive index
- 20 · n20/D 1.454(lit.)
- FLAVIS Number
- 8.036 · 08.036 | Citronellic acid
- Flash point
- 230 °F · >230 °F
- storage temp.
- 2 · Storage temp. 2-8°C
- solubility
- Almost insoluble in water, soluble in tslcohol and oils.
- pka
- 4.78 · 4.78±0.10(Predicted)
- form
- clear liquid
- color
- Colorless to Light yellow
- Odor
- Faint, fresh-green, somewhat grassy odor
- Odor Type
- green
- biological source
- synthetic
- Water Solubility
- Insoluble in water.
- JECFA Number
- 1221 · 1221
- Cosmetics Ingredients Functions
- ANTI-SEBORRHEICANTIMICROBIALFRAGRANCE
- InChI
- 1S/C10H18O2/c1-8(2)5-4-6-9(3)7-10(11)12/h5,9H,4,6-7H2,1-3H3,(H,11,12)
- InChIKey
- GJWSUKYXUMVMGX-UHFFFAOYSA-N
- SMILES
- CC(CC\C=C(\C)C)CC(O)=O
- LogP
- 3.35 · 3.35
- CAS DataBase Reference
- 502 · 502-47-6(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- 3 · 3,7-DIMETHYL-6-OCTENOIC ACID
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 1 JJT408R87 · 1JJT408R87
- EPA Substance Registry System
- 6 · 6-Octenoic acid, 3,7-dimethyl- (502-47-6)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 311 · H311-H315
- Precautionary statements
- 280 · P280-P302+P352+P312
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- Xn
- Risk Statements
- 21 · 21-38
- Safety Statements
- 36 · 36/37
- RIDADR
- 2810 · UN 2810 6.1/PG 3
- WGK Germany
- 3 · 3
- RTECS
- 3230000 · RH3230000
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1
- PackingGroup
- III
- HS Code
- 29161995 · 29161995
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 3 DermalSkin · Acute Tox. 3 DermalSkin Irrit. 2
Safety & regulation
GHS classification
GHS Classification
Danger
H311 (> 99.9%): Toxic in contact with skin [Danger Acute toxicity, dermal]
P262, P264, P270, P280, P302+P352, P316, P321, P361+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1635 reports by companies from 6 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: 6-Octenoic acid, 3,7-dimethyl-
Regulation (EC) No 1831/2003 (amended)
6-Octenoic acid, 3,7-dimethyl-: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryA moderate skin irritant; [RTECS] Safe when used as a flavoring agent in food; [JECFA] A skin irritant; Toxic by skin absorption; [Sigma-Aldrich MSDS] See Citronellol.
Hazard Classes and CategoriesAcute Tox. 3 (> 99.9%)
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- RH3230000
- ridadr
- UN 2810 6.1/PG 3
- hs_code
- 29161995
- risk_code
- 21-38
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- Xn
- safety_code
- 36/37
- hazard_class
- 6.1
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- packing_group
- III
- Hazard statements
- H311-H315
- Hazard Classifications
- Acute Tox. 3 DermalSkin Irrit. 2
- Precautionary statements
- P280-P302+P352+P312
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Uses & manufacturing
UsesUsed as a flavoring agent; [FDA]
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing Information6-Octenoic acid, 3,7-dimethyl-: ACTIVE
Applications
OccurrenceThe d-form is reportedly a constituent of Java citronella, geranium, Borosma pulchellum, Xanthoxylum piperitum, bitter-orange leaves, lemongrass, Calytrix virgata and Calytrix tetragona leaves; the l-form has been reportedly identified in cypress oil (Callitirs glauca R. Br.), Callitirs intratropica, in the oil of Chamaecyparis obtusa and of Thujopsis dolabrata; the d,l-form is isolated from camphor oil. Also reported found in mandarin peel oil, swangi (Citrus hystrix D.C.), peppermint oil and black tea.
UsesCitronellic acid was used in synthesis of stereoisomers of 3,11- dimethylnonacosan-2-one and 29-hydroxy-3,11-dimethylnonacosan-2-one.
Preparation methods
PreparationBy oxidation of citronellal; also by the conversion of pulegone.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers61 total
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
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Shaanxi Didu New Materials Co. Ltd+86-86-17392712779 +86-13289823923 · [email protected]
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TCI Chemicals (India) Pvt. Ltd.[email protected]
Hebei Chuanghai Biotechnology Co., Ltd+86-15350571055 · [email protected]
Additional notes
DefinitionChEBI: Citronellic acid is a monounsaturated fatty acid that is oct-6-enoic acid carrying methyl groups at positions 3 and 7. It has a role as a plant metabolite and a flavouring agent. It is a monoterpenoid, a medium-chain fatty acid and a monounsaturated fatty acid. It is functionally related to a citronellal.
Related reactions
26 records
Compound notes
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