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Views: 0 Author: Site Editor Publish Time: 2026-08-04 Origin: Site
Cinnamic acid (CAS 140-10-3 for trans-isomer; CAS 621-82-9 for the natural form) is an unsaturated aromatic carboxylic acid with the molecular formula C₉H₈O₂ and a molecular weight of 148.16 g/mol. It occurs naturally in cinnamon bark oil, storax balsam, and shea butter, and is produced industrially at scale via the Perkin reaction or Knoevenagel condensation.
At room temperature, it appears as white to off-white monoclinic crystals with a characteristic honey-like, balsamic odor. It is slightly soluble in water (~500 mg/L) but freely soluble in ethanol, ether, and most organic solvents.
Quick Facts |
|
IUPAC Name | (2E)-3-Phenylprop-2-enoic acid |
Common Synonyms | trans-Cinnamic acid, 3-Phenylacrylic acid, Benzenepropenoic acid |
CAS Number | 140-10-3 (trans); 621-82-9 (natural) |
EC Number | 205-398-1 |
FEMA Number | 2288 |
Molecular Formula | C₉H₈O₂ |
Molecular Weight | 148.16 g/mol |
Natural Sources | Cinnamon bark, storax balsam, shea butter |
Chemical Identity & Physical Properties
Property | Value |
Appearance | White to pale yellow monoclinic crystals or crystalline powder |
Odor | Honey-like, sweet-balsamic |
Molecular Weight | 148.16 g/mol |
Melting Point | 132–135 °C |
Boiling Point | 300 °C |
Density | 1.2475 g/cm³ |
Flash Point | >100 °C (closed cup) |
pKa | 4.44 |
Water Solubility | ~500 mg/L at 25 °C |
Solubility (Ethanol) | Freely soluble |
Solubility (Ether) | Freely soluble |
Log P (octanol/water) | 2.13 |
UV Absorption λmax | ~273 nm (in ethanol) |
This is the single largest application segment, accounting for an estimated 35–40% of global consumption.
As a direct flavoring agent, cinnamic acid (FEMA 2288) imparts a sweet, balsamic, honey-like note and is listed in:
FDA 21 CFR §172.515
● — Synthetic flavoring substances and adjuvants
EU Flavourings Regulation (EC) No 1334/2008
● — approved for all categories of flavored foods
FCC (Food Chemicals Codex)
● — minimum purity ≥99.0%
Ester derivatives represent the bigger-volume opportunity. Cinnamic acid is the precursor to three major fragrance esters:
Ester | CAS Number | Odor Profile | Primary Use |
Methyl cinnamate | 103-26-4 | Fruity, strawberry-like | Fragrance compositions, flavoring |
Ethyl cinnamate | 103-36-6 | Sweet, cinnamon, fruity | Perfumery; natural component of cinnamon oil |
Benzyl cinnamate | 103-41-3 | Balsamic, floral | Fixative in heavy floral perfumes |
Cinnamyl cinnamate | 122-69-0 | Mild balsamic | Fixative, blending agent |
These esters are widely used in fine fragrances, personal care products, household air care, candles, and industrial odorants for the flavor and fragrance (F&F) industry.
Perfumery application levels (typical):
● Fine fragrance: 0.5–5% of concentrate
● Functional fragrance (soap, detergent): 0.1–2%
● Flavor compounding: 1–50 ppm in finished food (varies by category)
Regulatory Status | Detail |
FDA GRAS | Listed as a flavoring agent and adjuvant under 21 CFR §172.515 |
FEMA GRAS | FEMA No. 2288 |
FCC Listed | Yes; purity ≥99.0%, melting range 132–135 °C |
EU Approved | FL No. 08.022; all food categories permitted |
JECFA | Evaluated; no safety concern at current intake levels |
Practical food applications include:
Baked goods & confectionery— imparts warm, sweet-balsamic undertones; often used in cinnamon, honey, and caramel flavor profiles
Beverages— carbonated soft drinks, alcoholic beverages (liqueurs), and flavored waters
Chewing gum— provides sustained sweetness and spice notes
Dairy & frozen desserts— ice cream, flavored yogurts
Synthetic sweetener precursor— cinnamic acid is enzymatically converted to L-phenylalanine, a key raw material for aspartame production
Cinnamic acid and its derivatives are registered for the following cosmetic functions under the EU Cosmetics Regulation (EC) No 1223/2009 and INCI nomenclature:
INCI Function | Mechanism / Role |
Perfuming | Provides sweet-balsamic scent; used in fragrance compositions for skin care, hair care, and fine fragrance |
Masking | Covers undesirable base odors in cosmetic formulations |
UV Absorber | Absorbs in the UVB range (~273 nm λmax); certain derivatives (e.g., octyl methoxycinnamate / octinoxate) are widely used as UV filters in sunscreens |
Skin Conditioning | Used as an emollient and conditioning agent in creams and lotions |
Hair Conditioning | Found in hair conditioners and styling products for shine and manageability |
Antioxidant | Scavenges free radicals; contributes to product stability and skin protection (as a cosmetic benefit, not a medical claim) |
Key derivatives in cosmetics:
Derivative | INCI Name | Cosmetic Use |
Octyl methoxycinnamate | Ethylhexyl Methoxycinnamate | UV-B filter in sunscreens (globally approved) |
Isoamyl p-methoxycinnamate | Amiloxate | UV-B filter |
Cinnamic acid esters (various) | — | Fragrance ingredients, fixatives |
The global cosmetics-grade cinnamic acid segment has grown steadily, driven by demand for naturally derived fragrance ingredients and the expanding sunscreen market in Asia-Pacific and Latin America.
Cinnamic acid serves as both a direct active ingredient and a synthesis intermediate in the agrochemical sector:
Direct agricultural applications:
Application | Mode of Action |
Herbicide | Certain cinnamic acid derivatives inhibit plant growth by interfering with phenylpropanoid metabolism |
Plant growth regulator | Modulates auxin-related pathways; used in tissue culture and crop management |
Fungicide / preservative | Post-harvest treatment for fruits; inhibits fungal spore germination |
Natural pesticide | Repellent and antifeedant activity against certain insect pests |
As a synthesis intermediate for agrochemicals:
Fluorinated cinnamic acid derivatives— building blocks for modern herbicides and fungicides
Cinnamic acid amides— precursors to crop protection agents
Cinnamaldehyde derivatives— produced from cinnamic acid reduction; used in biopesticide formulations
Beyond end-use applications, cinnamic acid is a workhorse intermediate in organic synthesis:
Downstream Product | Process | End Market |
Methyl / Ethyl / Benzyl cinnamate | Esterification | Fragrance, flavor |
Cinnamaldehyde | Reduction | Flavor, fragrance, agrochemical |
Cinnamyl alcohol | Further reduction | Fragrance fixative |
L-Phenylalanine | Enzymatic amination | Aspartame (sweetener) production |
Synthetic indigo | Multi-step conversion | Textile dye |
Cinnamic acid polymers | Photo-dimerization | Photo-resists, liquid crystal alignment layers, electronics |
Fluorocinnamic acids | Halogenation | Agrochemical & functional material intermediates |
The photo-dimerization property of cinnamic acid is particularly notable in materials science: under UV irradiation, trans-cinnamic acid undergoes [2+2] cycloaddition to form truxillic and truxinic acids — a reaction exploited in photolithography and liquid crystal display (LCD) manufacturing.
Commercial Grades & Specifications
Cinnamic acid is traded in several commercial grades, each targeting a specific end-use sector.
Grade | Purity (min.) | Key Specifications | Typical Packaging |
Food Grade (FCC) | ≥99.0% | Complies with FCC monograph; heavy metals ≤10 ppm; melting range 132–135 °C; residual solvents within limits | 25 kg fiber drum / 25 kg PE-lined paper bag |
Cosmetic Grade | ≥99.0% | Meets EU Cosmetics Regulation purity criteria; microbial limits controlled | 25 kg fiber drum |
Industrial / Technical Grade | ≥98.0–98.5% | Suitable for synthesis and non-food applications; wider impurity tolerance | 25 kg / 50 kg fiber drum; 500 kg supersack |
Natural Grade | ≥99.0% | Extracted from natural sources (cinnamon, storax); certified natural per ISO 16128 | 10–25 kg packaging |
Safety, Handling & Storage
Hazard Category | Classification |
Skin irritation | Category 2 (H315: Causes skin irritation) |
Eye irritation | Category 2A (H319: Causes serious eye irritation) |
Respiratory irritation | Category 3 (H335: May cause respiratory irritation) |
Signal Word | Warning |
Operation | Recommended PPE |
Laboratory handling | Lab coat, nitrile gloves, safety goggles |
Production / weighing | Dust mask (N95/FFP2), chemical-resistant gloves, safety goggles, protective clothing |
Spill response | Full PPE as above + respiratory protection if ventilation inadequate |
● Store in a cool, dry, well-ventilated area
● Keep container tightly closed when not in use
● Recommended storage temperature:15–25 °C
● Protect from direct sunlight and UV exposure (to prevent photo-dimerization)
● Avoid contact with strong oxidizing agents and strong bases
● Shelf life: typically 24–36 months from date of manufacture when stored properly
Exposure Route | Immediate Action |
Skin contact | Wash with plenty of soap and water. Remove contaminated clothing. |
Eye contact | Rinse cautiously with water for at least 15 minutes. Remove contact lenses if present. Seek medical attention if irritation persists. |
Inhalation | Move to fresh air. If breathing is difficult, seek medical attention. |
Ingestion | Rinse mouth. Do NOT induce vomiting. Seek medical attention. |
Cinnamic acid is primarily used in three sectors: (1) as a flavoring agent (FEMA 2288) and precursor to fragrance esters (methyl, ethyl, benzyl cinnamate) in the flavor and fragrance industry; (2) as a perfuming, UV-absorbing, and skin-conditioning ingredient in cosmetics; and (3) as a synthesis intermediate for agrochemicals, L-phenylalanine (for aspartame), synthetic indigo, and functional materials.
Both. Cinnamic acid occurs naturally in cinnamon bark, storax balsam, and shea butter. However, the vast majority of commercial cinnamic acid is synthetically produced via the Perkin reaction or Knoevenagel condensation to meet industrial volume demand. Natural-grade cinnamic acid (extracted from botanical sources) is available at a premium price for brands requiring natural certification.
Trans-cinnamic acid is the thermodynamically stable geometric isomer and the standard commercial form. When you purchase "cinnamic acid" from any supplier, you are buying trans-cinnamic acid (CAS 140-10-3) with a melting point of 132–135 °C. The cis isomer (allocinnamic acid, CAS 102-94-3) melts at ~68 °C, is less stable, and is not typically supplied as an article of commerce.
Yes. Cinnamic acid is listed as FEMA GRAS (No. 2288) and is approved by the FDA under 21 CFR §172.515 as a synthetic flavoring substance. It is also listed in the Food Chemicals Codex (FCC) with a minimum purity specification of ≥99.0%. When purchasing for food or beverage use, always specify "Food Grade / FCC grade."
Cinnamic acid has a characteristic honey-like, sweet-balsamic odor. Its esters have more pronounced and varied odor profiles: methyl cinnamate smells fruity (strawberry-like), ethyl cinnamate smells sweet-cinnamon, and benzyl cinnamate is balsamic-floral.
Store cinnamic acid in a cool (15–25 °C), dry, well-ventilated area in tightly closed containers. Protect from direct sunlight and UV light, as cinnamic acid can undergo photo-dimerization under UV exposure. Avoid proximity to strong oxidizing agents and strong bases. Typical shelf life is 24–36 months under proper storage conditions.
-Cinnamic acid (standard commercial form):CAS 140-10-3
Natural cinnamic acid:CAS 621-82-9
-Cinnamic acid (allocinnamic acid):CAS 102-94-3
Synthetic cinnamic acid is not permitted in USDA Organic or EU Organic certified products. However, naturally extracted cinnamic acid (from cinnamon, storax, etc.) may be used in organic formulations, provided the extraction process and carrier solvents comply with organic certification standards. Always verify with your certifier.
Cinnamic acid is classified as a mild irritant (GHS07: Warning). It may cause skin irritation (H315), serious eye irritation (H319), and respiratory irritation (H335). Standard PPE (gloves, goggles, lab coat) is sufficient for routine handling. It is not classified as carcinogenic, mutagenic, or reprotoxic. For detailed safety information, always consult the supplier's Safety Data Sheet (SDS).
Cinnamic acid is a versatile aromatic carboxylic acid with deep roots in both natural product chemistry and modern industrial manufacturing. Its established applications in flavors, fragrances, food, cosmetics, agriculture, and materials science — combined with a growing market projected to reach over USD 1 billion — make it a strategically important intermediate across multiple supply chains.
