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HCID 11089생성일: 2026년 10월 26일

무수트리멜리트산

무수트리멜리트산 · 트리멜리틱안하이드리드 · 트라이멜리트산무수물 · 트라이멜리트무수물 · 트라이멜리트산 무수물 · 1,2,4-벤젠트라이카복실산 무수물 · 1,2,4-벤젠트라이카복실산, 시클리 1,2-무수물 · 1,3-디옥소-5-프탈란카복실산

https://huagongshe.com/ko/chemical/11089

무수트리멜리트산 분자 구조식

식별자 및 물리적 특성

CAS No.552-30-7
분자식C9H4O5
평균 분자량192.12 g/mol
단동위원소 질량192.00587323 g/mol
SMILESO=C(O)c1ccc2c(c1)C(=O)OC2=O
InChIKeySRPWOOOHEPICQU-UHFFFAOYSA-N
PubChem CID11089
ChEMBLCHEMBL2137687
ChEBICHEBI:53050
EC No.209-008-0
DTXSIDDTXSID7026235
현지명무수트리멜리트산

화학 및 물리적 성질

XLogP0.8
극성 표면적80.7
수소 결합 공여자 수1
수소 결합 수용자 수5
회전 가능 결합 수1
무거운 원자 수14
형식 전하0
복잡도308
PolymersPlastics & Rubber -> Acid Anhydrides, Cyclic
SpringerMaterials PropertiesBoiling point
밀도1.55 at 68 °F (NTP, 1992) - Denser than waterwill sink1.54
Color/FormCrystalsColorless solid
용해도less than 1 mg/mL at 68 °F (NTP, 1992)Sol at 25 °C: 0.002 g/100 g carbon tetrachloride0.06 g/100 g ligroin0.4 g/100 g mixed xylenes15.5 g/100 g dimethyl formamide49.6 g/100 g acetone21.6 g/100 g ethyl acetate36.5 g/100 g 2-butanone at 25 °C38.4 g/100 g cyclohexanone at 25 °C0.06 g/100 g mineral spirits at 25 °CSolubility in water: reaction24.4g/l(분해)
인화점440.6 °F (NTP, 1992)227 °C o.c.
끓는 점464 to 473 °F at 14 mmHg (NTP, 1992)390 °CBoiling point: 240-245 °C at 14 mm HgBoiling point 240-245 °C at 14 mm Hgat 1.87kPa: 240-245 °C464-473 °F at 14 mmHg
DecompositionWhen heated to decomposition it emits acrid smoke and irritating fumes.
녹는점329 to 336 °F (NTP, 1992)161-163.5 °C329-336 °F322 °F163-166 °C (lit.)
증기 밀도6.6 (NTP, 1992) - Heavier than airwill sink (Relative to Air)Relative vapor density = 6.6 (air =1)Relative vapor density (air = 1): 6.66.6 (vs air)
증기압4e-06 mmHg at 77 °F (NTP, 1992)0.00000986 [mmHg]Vapor pressure: 4X10-6 mm HgVapor pressure of liquid trimellitic anhydride = 2.25 mm Hg at 200 °CVapor pressure at 25 °C: negligible0.000004 mmHg<0.01 mm Hg ( 20 °C)
Food Contact SubstancesFCS -> FDA Cumulative Estimated Daily Intake (CEDI)FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFRFCS -> FDA Inventory of Effective Food Contact Substance (FCS) Notifications
굴절률1.4717 (estimate)
저장 조건Store below +30°C.
pKa(산도 계수)3.11±0.20(Predicted)
물리적 상태플레이크
색상흰색에서 황백색까지
pH2 (21g/l, H2O, 20℃)
폭발한계1-7%(V)
용해도물에서 분해되다
Merck14,9703
BRN9394
안정성안정적인. 수분에 민감합니다.
InChI1S/C9H4O5/c10-7(11)4-1-2-5-6(3-4)9(13)14-8(5)12/h1-3H,(H,10,11)
InChIKeySRPWOOOHEPICQU-UHFFFAOYSA-N
SMILESOC(=O)c1ccc2C(=O)OC(=O)c2c1
LogP(분배 계수)0.06-0.54 at 20℃
NISTTrimellitic anhydride(552-30-7)
EPATrimellitic anhydride (552-30-7)

화학적 성질

Trimellitic anhydride is a white powder or flakes. It is the anhydride of trimellitic acid (1,2,4-benzenetricarboxylic acid). It is soluble in water, ethanol, acetone and other general organic solvents.

안전 및 규제

GHS 분류DangerH317: May cause an allergic skin reaction [Warning Sensitization, Skin]P233, P260, P261, P264+P265, P271, P272, P280, P284, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P333+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1477) of reports.H317 (99.9%): May cause an allergic skin reaction [Warning Sensitization, Skin]
규제 정보Chemical: 5-Isobenzofurancarboxylic acid, 1,3-dihydro-1,3-dioxo-Hazard Traits - Respiratory ToxicityCouncil Directive (EEC) No 109/1989 (Repealed by Reg. EC No 1935/2004 (amended))5-Isobenzofurancarboxylic acid, 1,3-dihydro-1,3-dioxo- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 5-Isobenzofurancarboxylic acid, 1,3-dihydro-1,3-dioxo- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 05-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15095Substance: Benzene-1,2,4-tricarboxylic acid 1,2 anhydride
기타 안전 정보IMAP assessments - 5-Isobenzofurancarboxylic acid, 1,3-dihydro-1,3-dioxo-: Environment tier I assessment
화재 위험This chemical is combustible. (NTP, 1992)Combustible. Finely dispersed particles form explosive mixtures in air.
화재 가능성Combustible.
건강 유해성Excerpt from NIOSH Pocket Guide for Trimellitic anhydride:
유해성 요약There are three syndromes caused by trimellitic anhydride (TMA) based on its ability to irritate and sensitize lung tissue. Sensitized workers can develop upon re-exposure 1) asthma-rhinitis2) late respiratory systemic syndrome (LRSS)or very rarely 3) pulmonary disease anemia syndrome (PDA). [Grammer LC et al. Review of trimellitic anhydride (TMA) induced respiratory response. Allergy Asthma Proc 1997 Jul-Aug18(4):235-7] Workers exposed to less than 0.002 mg/m3 are at low risk for developing disease. [Grammer LC et al. A Clinical and Immunologic Study to Assess Risk of TMA-Induced Lung Disease as Related to Exposure. JOEM 1999 Dec41(12):1048-51] TMAN is a potent sensitizer after inhalation of either dust or fume. It causes IgE and IgG mediated disease (asthma/rhinitis, late respiratory systemic syndrome, pulmonary disease anemia, and late arthralgia myalgia). Symptoms include sneezing, rhinitis, dry throat, watery eyes, conjunctivitis, and dyspnea. Dermal contact may cause or exacerbate respiratory sensitization. When workers are not exposed to >2 ug/m3, there are no cases of disease or IgG against TM-HAS (Human Serum Albumin), but there are still cases of non-diseased workers with IgE against TM-HAS (9% incidence). TMAN cause both immediate and delayed dermal sensitization in animal studies. [ACGIH] Danger of airway sensitization[MAK] TMA skin testing provides an alternative and potentially more practical method for monitoring TMA-exposed workers for developing IgE sensitization. [PMID 21915071] See ACID ANHYDRIDES.
반응성 그룹Acids, Carboxylic
EC 분류Symbol: XnR: 37-41-42/43S: (2)-22-26-36/37/39
Special ReportsEuropean Chemicals BureauIUCLID Dataset, Benzene-1,2,4-tricarboxylic acid 1,2-anhydride (CAS No.552-30-7) (2000 CD-ROM edition). Contains information on usage patterns, toxicology, and ecological effects submitted by industry to the European Union. Available from the database query page: http://ecb.jrc.it/esis/esis.php as of August 28, 2006.
Reactivity ProfileTRIMELLITIC ANHYDRIDE reacts exothermically with water. This reaction is expected to be slow, but can become vigorous if local heating accelerates it. Reaction with water is accelerated by acids. Incompatible with acids, strong oxidizing agents, alcohols, amines, and bases. Incompatible with strong oxidizing agents, strong acids or strong bases. (NTP, 1992).
Chemical DangersReacts violently with bases and oxidants. Reacts slowly with water. This produces trimellitic acid.
Flammable LimitsCombustible Solid
소화Fires involving this material should be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)Use water spray, powder.
응급 조치Fresh air, rest. Refer for medical attention.Remove contaminated clothes. Rinse skin with plenty of water or shower.First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .
응급 처치EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.(General first aid procedures)
안전 보관Dry. Separated from bases and strong oxidants. Ventilation along the floor.
Firefighting Hazards... If dry, it can be charged electrostatically by swirling, pneumatic transport, pouring, etc ... A harmful concentration of airborne particles can be reached quickly when dispersed.
노출 관리 및 개인 보호0.04 [mg/m3]
소화 절차Water spray, powder.
보관 조건Dry. Separated from bases and strong oxidants. Ventilation along the floor.
정리 방법Personal protection: P3 filter respirator for toxic particles. Sweep spilled substance into containersif appropriate, moisten first to prevent dusting. Carefully collect remainder.
비화재 누출 대응SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
처리 방법SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations.
누출 처리Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder.
체내 부담Personal breathing zone samples from two workers in a 55-gallon drum manufacturing plant had an 8 hour exposure to trimellitic anhydride of 3.6 mg/cu-m and 1.7 mg/cu-m(1).
상호 작용... Ozone (3 ppm for 3 hr) caused an increase in -log PC300 at 1 hr after exposure, with return of -log PC300 to control levels at 8 hr. Ozone also increased baseline RL at 8 hr. trimellitic anhydride (TMA) challenge increase -log PC300 in TMA-sensitized guinea pigs at 8 hr after challenge from 3.85 +/- 0.09 to 4.11 +/- 0.09. Ozone exposure prior to TMA challenge prevented the induction of airway hyperresponsiveness with a mean -log PC300 of 3.51 +/- 0.20, which was not different from that of control TMA-sensitized group. Baseline lung resistance was significantly higher in ozone-pretreated animals after TMA challenge when compared to those of either control or challenged with TMA alone. Ozone had no effect on TMA challenge-induced BAL eosinophilia and neutrophilia.... Before challenge, sensitized animals were pretreated iv with inhibitors of different mediators: pyrilamine (antihistamine: 2 mg/kg, indomethacin (cyclooxygenase inhibitor: 10 mg/kg), OKY-046 (thromboxane synthetase inhibitor: 30 mg/kg), ICI-198,615 (leukotriene receptor antagonist: 10-6 mol/kg), ketanserin (5-HT2 receptor antagonist: 1 mg/kg), or azelastine ("antiallergic agent": 1 mg/kg). Intratracheal instillation of trimellitic anhydride conjugated to guinea pig serum albumin (TMA-GPSA) induced a slowly progressing increase in lung resistance (RL) and produced extravasation of Evans blue dye at all airway levels in sensitized animals. Pyrilamine and azelastine abolished the increase in RL induced by TMA-GPSA until 2.5 min after the challenge. Indomethacin and OKY-046 significantly attenuated the increase in RL 3 min after the challenge. ICI-198,615 and ketanserin did not significantly affect the increase in RL. Extravasation of Evans blue dye induced by TMA-GPSA was decreased by pyrilamine, azelastine and ICI-198,615 in main bronchi and intrapulmonary airways. Indomethacin, OKY-046 and ketanserin did not significantly affect the extravasation of dye into the airway tissue.... Both IgE and IgG anti-trimellitic anhydride antibodies started to rise between weeks 1 and 3 after immunisation, reached their highest levels 7 weeks after sensitisation with 3% of TMA and then started to decline. Betamethasone and cyclosporin A (CsA) given orally over the time of sensitisation (8 days in total) inhibited the development of specific IgE and IgG anti-TMA antibodies. Betamethasone given 10-17 days after sensitisation attenuated the IgE and IgG antibody responses as well while treatment with CsA after sensitisation had no effect on the production of specific antibodies. Levels of total IgE and IgG were not affected except for a small decrease in total IgE using medium-dose betamethasone after sensitisation.... Guinea pigs pretreated with cobra venom factor (CVF) had significantly reduced amounts of complement component C3 in the lavage fluid 24 hours after trimellitic anhydride (TMA) conjugated to guinea pig serum albumin challenge. Pretreatment with CVF did not affect the immediate TMA-induced bronchoconstriction nor the TMA-induced microvascular leakage. In animals depleted of the complement system by pretreatment with CVF the TMA-induced increase in mononuclear cells, total white blood cells, red blood cells, and EPO activity in the bronchoalveolar lavage was significantly reduced.... Exposure to 0.5 mg/cu m trimellitic anhydride produced hemorrhagic foci of the lung and increased antibody levels in rats treated for six hours/day, five days/week for two weeks ... Estrogen treatment reduced the number of lung foci in both male and female rats, while testosterone treatment had no effect.
표적 장기Eyes, skin, respiratory system
환경 거동TERRESTRIAL FATE: Based on the structural similarities to phthalic anhydride, trimellitic anhydride is expected to have a similar hydrolysis rate(SRC). Phthalic anhydride has been reported to hydrolyze rapidly in water(1) and estimated half-lives of approximately 1.5 minutes and 2.7 minutes were calculated(SRC) using reported observed rate constants of 7.9X10-3/sec(2) and 4.3X10-3/sec(3), respectively. Based upon this hydrolysis rate, trimellitic anhydride is expected to hydrolyze in moist soils(SRC). Volatilization from soil surfaces and adsorption to soil are not expected to be important processes because of hydrolysis(SRC).AQUATIC FATE: Based on the structural similarities to phthalic anhydride, trimellitic anhydride is expected to have a similar hydrolysis rate(SRC). Phthalic anhydride has been reported to hydrolyze rapidly in water(1) and estimated half-lives of approximately 1.5 minutes and 2.7 minutes were calculated(SRC) using reported observed rate constants of 7.9X10-3/sec(2) and 4.3X10-3/sec(3), respectively. Therefore, volatilization from water surfaces, adsorption to suspended solids and sediments, biodegradation, and bioconcentration of trimellitic anhydride are not expected to be important in aquatic systems based on hydrolysis(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), trimellitic anhydride, which has an extrapolated vapor pressure of 9.86X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase trimellitic anhydride is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 20 days(SRC), calculated from its rate constant of 7.97X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase trimellitic anhydride may be physically removed from the air by wet and dry deposition(SRC).
유해 작용Hemolytic anemia - Decreased hemoglobin or number of red blood cells.
노출 경로The substance can be absorbed into the body by inhalation and by ingestion.inhalation, ingestion, skin and/or eye contact
생태독성 발췌/AQUATIC SPECIES/ No signs of toxicity were observed in Daphnia magna (water flea) exposed to TMA/TMLA nominal concentrations of 130, 220, 350, 600, or 1,000 mg/L for 48 hours under static conditions ... Based on measured concentrations, the 96 hr NOEC was > 792 mg/L./AQUATIC SPECIES/ No signs of toxicity were observed in Scenedesmes subspicatus (green algae) exposed to TMA/TMLA nominal concentrations of 62.5, 125, 250, 500, or 1,000 mg/L for 96 hours under static conditions ... Based on measured concentrations, the NOEC was > 739 mg/L./AQUATIC SPECIES/ No signs of toxicity were observed in Leuciscus idus melanotus (Golden Orfe) exposed to TMA/TMLA nominal concentrations of 130, 220, 350, 600, or 1,000 mg/L for 96 hours under static conditions ... Based on measured concentrations the 96 hour NOEC > 896 mg/L./AQUATIC SPECIES/ Because TMA rapidly hydrolyzes to form trimellitic acid (TMLA) in water, following pH adjustment TMLA and sodium trimellitate salts are the actual form of the chemical evaluated in aquatic toxicity tests.
Signs and SymptomsCough. Headache. Nausea. Shortness of breath. Wheezing. Symptoms may be delayed.Redness. Pain.Nausea. Abdominal pain. Burning sensation. Vomiting. Diarrhoea.irritation eyes, skin, nose, respiratory systempulmonary edema, resp sensitizationrhinitis, asthma, cough, wheezing, dyspnea (breathing difficulty), malaise (vague feeling of discomfort), fever, muscle aches, sneezing
Ongoing Test StatusThe following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=552-30-7]
Medical SurveillanceThis article described our clinical and immunologic experience in assessing workers exposed to trimellitic anhydride (TMA) in three industrial settings. Since 1977 /the authors/ have had engaged in a prospective study of workers involved at the site of manufacture of TMA. These studies demonstrate that serologic measurements of total antibody to trimellityl human serum albumin (TM-HSA) and IgE antibody to TM-HSA are predictive of the development of an immunologically mediated respiratory illness and are useful in monitoring workers removed from TMA exposure, in identifying asymptomatic workers who may be at risk in the future, and in defining the nature of sensitization of the work force. In a different industrial setting, /the authors/ have been able to study workers who mixed previously manufactured TMA powder with epoxy resins. This study indicated that clinical assessments by a plant physician with a standardized questionnaire, along with serologic tests, could establish the presence or absence of an immunologic respiratory illness caused by the inhalation of TMA dust. In a third industrial situation, workers were exposed to both TMA and phthalic anhydride (PA). Here workers were interviewed by a local physician with minimal experience with TMA-related respiratory illness. In this situation a more detailed questionnaire was utilized, along with serologic tests utilizing the enzyme-linked immunosorbent assay to establish the presence of a TMA- or PA-related syndrome. Immunologic studies demonstrated in workers exposed to both TMA and PA that the antibody responses elicited showed little crossreactivity between antibodies directed against TM-HSA or PA-HSA.... A practical approach that has significantly reduced the incidence of immune disease due to trimellitic anhydride is periodic surveillance of exposed worker populations with serum antibody studies and questionnaires. Workers who have significant levels of antibody, report significant symptoms on questionnaires, or both, are further evaluated to determine the clinical diagnosis and whether any interventions are needed.
Soil Adsorption/MobilityBased on the structural similarities to phthalic anhydride, trimellitic anhydride is expected to have a similar hydrolysis rate(SRC). Phthalic anhydride has been reported to hydrolyze rapidly in water(1) and estimated half-lives of approximately 1.5 minutes and 2.7 minutes were calculated(SRC) using reported observed rate constants of 7.9X10-3/sec(2) and 4.3X10-3/sec(3), respectively. Based upon this hydrolysis rate, trimellitic anhydride adsorption to soil and leaching are not expected to be important processes(SRC).
TSCA Test SubmissionsTrimellitic anhydride (CAS# 552-30-7) was evaluated for teratogenicity. The test substance was administered via inhalation to pregnant rats during gestation days 6-15 for 6/hrs/day at a concentration of 500 ug/cu m. Half of the animals were sacrificed for pathological evaluation and the other half were given a single "challenge" exposure of 500 ug/cu m for 6-hours. Pathological findings concluded there was a significant increased in the number of hemorrhagic lung foci and an increased level of trimellitic anhydride (TMA) specific serum antibody in all rats. There were no significant treatment-related differences in litter size, litter viability, variations, or malformations.Trimellitic anhydride (CAS# 552-30-7) was evaluated for teratogenicity. The test substance was administered via inhalation to pregnant guinea pigs during gestation days 6-26 for 6/hrs/day at a concentration of 500 ug/cu m. Half of the animals were sacrificed for pathological evaluation and the other half were given a single "challenge" exposure of 500 ug/cu m for 6-hours. Pathological findings concluded there was a significant increase in the number of hemorrhagic lung foci and an increased level of trimellitic anhydride (TMA) specific serum antibody in 2/7 guinea pigs. There were no significant differences in litter size, litter viability, variations, or malformations.Subchronic inhalation toxicity and sensitization potential were evaluated in groups of 15 rats (sex and strain not reported) exposed to a single 6-hour dose of trimellitic anhydride at a level of 0, 0.3, 1.6, 7.7, 23.9 or 135 micrograms/cu m with a second 6-hour dose to 500 micrograms/cu m 3 weeks later. The method of atmosphere generation and compound concentration measurement was not reported. There were no mortalities or clinical observations reported. Necropsy revealed a dose-dependent increase in hemorrhagic foci in the lungs of treated animals.
직업 노출 등급(OEB)D
직업 노출 한계(OEL)TWA: 0.005 ppm (0.04 mg/m3) Should be handled in the workplace as an extremely toxic substance.
수질 위해 등급(WGK)1
TSCA 등재 상태TSCA listed
RTECS 번호DC2050000
독성LD50 orally in Rabbit: > 2730 mg/kg LD50 dermal Rabbit 23000 mg/kg
관세 코드29173980
위험 문구(R)37-41-42/43
위험 표시Xn
안전 문구(S)22-26-36/37/39
기존화학 물질KE-10640
F 고인화성물질10-21
위험 등급Eye Dam. 1Resp. Sens. 1Skin Sens. 1STOT SE 3
저장 분류11 - Combustible Solids
유해 물질 데이터552-30-7(Hazardous Substances Data)
중점관리물질 필터링별표1-87

용도

용도

Trimellitic Anhydride is mainly used as raw material for polyester resin,polyimide resin,plasticizer TOTM ,and also be used for producing heatproof & insulating,adhesive,surfactant, paint,synthesize dye materials etc. Trimellitic anhydride is used as an embossing agent for vinyl flooring and as a curing agent for epoxy resins. It is also used as an intermediate for the synthesis of surface coatings chemicals, adhesives, polymers, dyes printing inks, pharmaceuticals .

일반 설명

1,2,4-Benzenetricarboxylic anhydride(TA) is a hydrophilic monomer with multipurpose usage; as a curing agent for epoxy based resins and as a plasticizer for polyvinyl chloride(PVC).